4-Bromoacetyl bromide

Bromoacetyl bromide Pyridine Suifuric acid Ammonia Potassium nitrate ... 

To a solution of 42 g of 2.amino.2 -chlorobenzophenone in 500 ml of benzene, 19 ml of bromoacetyl bromide was added dropwise. After refluxing for 2 hours, the solution was cooled, washed with 2N sodium hydroxide and evaporated. The residue was recrystallized from methanol giving crystals of 2-bromo.2. (2-chlorobenzoyl) acetanilide melting at 119° to 121°C. 

Bromoacetyl bromide Potassium nitrate Sodium hydride... 

A solution of 21.5 grams of 2-amino-2 -fluorobenzophenone in 500 cc of ether was treated with 20 cc of a 20% (v/v) solution of bromoacetyl bromide in ether. The mixture was shaken and allowed to stand for 5 minutes and then washed with water (20 cc). The proc-... 

Timolol maleate a-Bromoacetophenone Nomifensine maleate Bromoacetyl bromide Bromazepam Cephapirin sodium Clonazepam Flunitrazepam 5-Bromoacetyl salicylamide Labetalol HCI m-Bromoanisole Tramadol HCI p-Bromoanisole Cyclofenil Bromobenzene... 

A stirred solution of methyl 2-(benzylamino)benzoate (12.6 g, 52 mmol) and pyridine (4.2 g, 53 mmol) in Et20 (500 inL) was slowly treated with bromoacetyl bromide (10.6 g, 52.5 mmol). Stirring was continued for 2 h, the precipitated pyridinium bromide was filtered off and the filtrate was evaporated under reduced pressure. The resulting syrupy methyl 2-[benzyl(bromoacetyl)aimno]benzoate was dissolved in MeOH (1 L) and the solution was saturated with NH, at 20 C and left for 8 h. The solution was evaporated in vacuo and the residue was crystallized (CH2C12/Et20) yield ll.Og (79%) mp 189-190 C. 

C8H7B1O 70-11-1) see Fendosal Hexocyclium metilsulfate Levamisole Nomifensine 4 -bromoacetophenone (CjH7BrO 99-90-1) see Zimeldine bromoacetyl bromide... 

Bromoacetic acid has been prepared by direct bromination of acetic acid at elevated temperatures and pressures,2-3-4 or with dry hydrogen chloride as a catalyst 6 and with red phosphorus as a catalyst with the formation of bromoacetyl bromide.6-7-8-9-19 Bromoacetic acid has also been prepared from chloroacetic acid and hydrogen bromide at elevated temperatures 6 by oxidation of ethylene bromide with fuming nitric acid 7 by oxidation of an alcoholic solution of bromoacetylene by air 8 and from ethyl a,/3-dibromovinyl ether by hydrolysis.9 Acetic acid has been converted into bromoacetyl bromide by action of bromine in the presence of red phosphorus, and ethyl bromoacetate has been... 

An alternative way of making cephapirin is the acylation of 7-aminocephalosporanic acid by bromoacetyl bromide, which gives a bromoacetyl derivative (32.1.2.5), and which is then reacted with 4-mercaptopyridine in the presence of triethylamine, forming the desired cephapirin (32.1.2.4) [75-78]. 

Chloroacetyl chloride and 2-bromoacetyl bromide N-acylated without a catalyst but 2-chloroacetic anhydride required concentrated sulfuric acid. ° 3-Chloro- and 3-bromopropionyl chlorides 9-acyl-ated without a catalyst as did cinnamoyl chloride " and phosgene, the last producing 9-chloroformyIcarbazole. ... 

Protection of the secondary alcohol as the corresponding methoxy methyl (MOM) ether, followed by removal of the Boc group with ZnBr2 in dichloromethane and acylation of the incipient secondary amine with bromoacetyl bromide in the presence of K2CO3 afforded the bromoacetamide 114 in 86% yield from 113. Treatment of 114 with methanolic ammonia afforded the corresponding glycinamide which was directly subjected to cyclization in the presence of NaH in toluene/HMPA to afford the bicyclic compound 115 in 79% overall yield from 114. Next, a one-pot double carbomethoxylation reaction was performed by the sequencial addition of n-BuLi in THF followed by addition of methylchloroformate, that carbomethoxylated the amide nitrogen atom. Subsequent addition of four equiv of methyl chloroformate followed by the addition of 5 equiv of LiN(TMS)2 afforded 116 as a mixture of diastereomers in 93% yield that were taken on directly without separation. 

Ruoho and Rong have descnbed a shorter route to salmeterol (Scheme 4). Friedel-Crafts acylation of salicylaldehyde (16) with bromoacetyl bromide in the presence of aluminum chloride gave the acetophenone 17. Alkylation of amine 18 with bromoacetyl 17 in refluxing acetonitrile gave the ketone 19. Reduction of 19 with sodium borohydride in methanol followed by catalytic hydrogenolysis of the benzyl group over 10% Pd/C gave salmeterol (2). 

The intercalated cationic radical initiator was synthesized from 2,2 -azobis[2-methyl-N-(2-hydroxyethyl) propionamide] by esterification with bromoacetyl bromide, and subsequent quaternization with tributylamine. Sodium montmorillonite was suspended in deionized water. The cationic radical initiator was bound onto the montmorillonite by ion exchange. 

Y-Vlethyl-4-fIuoroanilinc (49.5 g. 0.395 mol) was added dropwise over 30 min to bromoacetyl bromide (40 g, 0.198 mol) dissolved in benzene (250 ml) and the mixture was stirred overnight. The solution was filtered and washed with dil. HC1 and then dried (Na2S04) and concentrated in vacuo. The residue was triturated with toluene and filtered. The toluene was removed and the residue distilled under vacuum to give the product as an oil (14.4 g, 30%). 

Coupling of bromoacetic acid To a stirred soln of bromoacetic acid (10 equiv) in CH2C12 (maximum concentration 0.3 M) were added bromoacetyl bromide (8 equiv) and DIPEA (20 equiv). The mixture was added to amino-peptide-resin and shaken for 10 min with the resin followed by washing with CH2C12. 

Ketene has also been formed by the action of zinc upon an ethereal solution of bromoacetyl bromide.5 Carbon monoxide and diazomethane, diluted with ether, when passed through a quartz tube at 400-500°, yield ketene and nitrogen.6... 

Note.—The bromoacetyl bromide and bromoacetic acid must not be allowed to touch the hands as they cause serious wo ends. 

Amino-8-oxo-3-vinyl-5-thia-l-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid 4-methoxyphenyl ester 4-Bromoacetyl bromide Sodium nitrite Trifluoroacetic acid... 

By interaction of 7-amino-8-oxo-3-vinyl-5-thia-l-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid 4-methoxyphenyl ester with 4-bromoacetyl bromide was prepared 7-(4-bromo-3-oxo-butyrylamino)-8-oxo-3-vinyl-5-thia-l-azabicyclo (4.2.0)oct-2-ene-2-carboxylic acid 4-methoxyphenyl ester. The active methylene group in that product was then nitrosated with sodium nitrite. The initial product spontaneously tautomerizes to afford 7-(4-bromo-2-hydroxyimino-3-oxo-butyrylamino)-8-oxo-3-vinyl-5-thia-l-azabicyclo(4.2.0) oct-2-ene-2-carboxylic acid 4-methoxyphenyl ester. By the reaction of that compound with thiourea and then with trifluoroacetic acid was obtained (6R,7R)-7-(2-(2-amino-4-thiazolyl)glyoxylamido)-8-oxo-3-vinyl-5-thia-l-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid sodium nitrite, (Z)-oxime (Cefdinir sodium nitrile). 

One route is that described in US Patent 3,422,100 as follows, starting with aminocephalosporanic acid (ACA) 27.2 g (0.1 mol) of 7-ACA, 33.2 g (0.3 mol) of NaHC03, 200 ml of water and 100 ml of acetone were mixed together, cooled to 0°C and stirred rapidly while 20.1 g (0.1 mol) of bromoacetyl bromide dissolved in 100 ml of acetone was added in one fast addition. The temperature was kept at 0 to 5°C for ten minutes, then the ice-salt bath was removed and stirring continued for one hour as the temperature approached 25°C. The mixture was concentrated in vacuo at 20°C to one-half volume and 200 ml of water added. Two 400 ml ether extracts were made and discarded. The aqueous solution was covered with 200 ml of ethyl acetate and vigorously stirred and cooled while being acidified to pH 2 with 40% phosphoric acid. 

Amino-2 -nitrobenzophenone Bromoacetyl bromide Sulfuric acid... 

As Scheme 68 illustrates, the first step of the reaction was the synthesis of the ferf-butyl ester 235 from bromoacetyl bromide 236. Owing to the... 

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