Bromoacetyl chloride

When bromoacetyl chloride is used instead of bromoacetic acid, the anilide 33 is formed at the first stage. Its subsequent cyclization also leads to 32. This approach to benzotellurazinone is similar to that developed for the synthesis of 2//-l,4-benzothiazin-3(4//)-ones (66CJC1247). Significantly, attempts to isolate the intermediate sulfonium salts analogous to 30 were unsuccessful. 

Next the product is acylated with bromoacetyl chloride and the glycine equivalent is constructed in place by a Gabriel amine synthesis (phthalamide anion followed by hydrazine) subsequent to which cyclization to benzodiazepine occurs. The synthesis of the tranquilizer quazepam (88) is finished by thioamide conversion with phosphorus pentasulfide. ... 

C2H2Br20 598-21-0) see Cefapirin Clonazepam Flunitrazepam Haloxazolam Ketazolam Sotalol bromoacetyl chloride... 

A more traditional cephalosporin analogue is cephapirin (22). It was made by reacting 7-aminocephalo-sporanic acid with bromoacetyl chloride to give amide 21. The halo group was displaced by 4-thiopyridine... 

Similarly, acylation of the dipeptide 410 with bromoacetyl chloride followed by base-induced cyclization gives the pyrazinylacetate ester 411 <2001BML1251>. Compound 410 is itself cyclized with />-toluenesulfonic acid to give the (iV-alkylated indole) equivalent of 406 <200JME3518>. 

The second way differs little from the previous, and consists of the initial formation of 4-hydroxy-3-acetoxybromoacetophenone (11.1.27) by acylation of methyl ester salicylic acid using bromoacetyl chloride. This is also reacted with iV-benzyl-tcrt-buty-lamine, and the resulting product (11.1.28) is completely hydrolyzed by lithium aluminum hydride into the (V-benzyl substituted albuterol (11.1.29), the benzyl group of which is removed by hydrogen over a palladium catalyst to give the desired albuterol (11.1.26) [31]. 

The intramolecular cyclization toward tetrahydroisoquinolines can lead to some interesting chemistry. The reaction of isothiocyanatocarbonyls with aromatic ethyl amines gives the fused systems under mild conditions (Seheme 47) <2003CHE277>. Reaction of thioamide derivatives with bromoacetyl chloride upon cyclization leads to A -acetaltetrahydroisoquinoline derivatives, which can be treated with Raney nickel to produce 38... 

Bromophenacyl bromide has been prepared by the interaction of bromobenzene and bromoacetyl chloride in the presence of aluminum chloride2 and by the bromination of -bromo-acetophenone.1,3... 

An alternative method for preparing derivatives of bromoacetate involves using bromoacetyl bromide or bromoacetyl chloride. The synthesis of the N-bromoacetyl derivative of L-arginine methyl ester with bromoacetyl bromide was carried out by Liu (1967). The product N-bromoacetyl-L-arginine methyl ester was a successful affinity label for streptococcal proteinase. L-Arginine methyl ester dihydrochloride (780 mg 3 mmoles) was dissolved in 6 ml of ice-cold 1 N NaHCOj. Over a period of 20 min, freshly distilled bromoacetylbromide, 3... 

The following procedure is useful for preparing " C-bromoacetyl chloride. (l- C)Bromoacetyl chloride was prepared by Hass and Neurath (1971a) by dissolving 693 mg of bromoacetic acid in 20 ml of anhydrous ether and then adding 1.0 gram of phosphorus penta-chloride. After all the PCI 5 had dissolved (about 1 hr) the solution was evaporated on a rotatory evaporator at 30°C. 

Ziegler and coworkers have reported several DFT studies on organometallic systems. Representative examples of this work include the study of (i) C-H bond activation by [(cp)M(L)] (M = Rh, Ir L = CO, PH3) and M(CO)4 (M = Ru, Os) [106], (ii) ketene forming reactions involving bromine abstraction from 2-bromoacetyl chloride by [Mn(CO)s]- [107], (iii) intermediates and reaction steps in the HCo(CO)4 catalysed hydroformylation reaction [108] as shown in Fig. 6, (iv) the role of the carbene L2Mo(X)CH2 and the molybdacyclobutane... 

Saima confirmed that 132 was readily obtained in ether in the cold. Sanna also prepared 3-bromoacetylindole (133) and 3-iodoacetylindole (134) by the action of bromoacetyl chloride and iodoacetyl chloride, respectively, on the indole Grignard reagent.The corresponding... 

S3. p-Chlorophenacyl Bromide. 2-Bromo-I-(4-chlo-rophenyltethanone 2-bromo-J ehloroacetophenone 4-chlo-ro -bromoocetophen One a - bromo -p-ch loroacetophenone. C-H[Pg.332]

Figure 3 Schematic potential diagram for photodissociation of bromoacetyle chloride, (a) The case when the upper A" states are neglected. The barrier heights cannot explain the dominant breakage of C—Cl bond, (b) Nonadiabatic tunneling type curve crossing scheme. This can explain the experimental fact. (From Ref. 12.)...

Reactions of Miscellaneous Haloketones and Acid Chlorides. - UV irradiation of fluorocarbonyl iodide results in the formation of (OCIF)... 1 and (OCFI)... F complexes,while ab initio methods have been used to interpret the photoreactivity of bromoacetyl chloride. A further study on the latter system has shown that the C-Cl bond ruptures on irradiation at 248 nm. " ... 

The starting material for the second route is methyl salicylate, which is treated with bromoacetyl chloride in a Friedel-Crafts acylation. The amine is then introduced as in the first synthesis, the ester and keto functions are reduced with lithium aluminium hydride, and the benzyl residue is finally cleaved off. 

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