1-Bromo-3-chloropropane

Phosphorus tribromide (271 g., 1.0 mole) is stirred and cooled in an ice bath while 189 g. (2.0 moles) of trimethylene chlorohydrin [Org. Syntheses Coll. Vol. 1, 533 (1941)] is added dropwise over a 2-hour period. The reaction mixture is protected from atmospheric moisture by a calcium chloride tube during this and the subsequent operation. The mixture is then heated on a water bath and stirred for 10 hours, after which it is cooled and poured into 11. of cold water. The organic layer is washed with 10% aqueous sodium carbonate 

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The NMR spectrum of 1 bromo 3 chloropropane contains 1 peaks at 8 30 8 35 and 8 43 Assign these signals to the appropriate carbons J... 

The requisite intermediate. 10-(3-chloropropyl)-2-acety(phenothiazine is prepared as follows To a suspension of sodamide (from 3 grams of sodium) in 300 ml of liquid ammonia is added 30 grams of 2-acetylphenothiazine. After stirring for one hour, there is added 19 grams of 1-bromo-3-chloropropane. The ammonia is allowed to evaporate and the residue is diluted with 200 ml of water. The mixture is extracted with ether and the ether solution is dried over anhydrous sodium sulfate, filtered and concentrated. 

N-[2-(3,1 -DioxanyDethyl] piperazine 1 -Bromo-3-chloropropane 2-Trifluoromethylphenothiazine Sodium Succinic acid... 

The 2-chloro-10-( y-chloropropyl)phenothiazine starting material is produced from 2-chloro-phenothiazine and 1 -bromo-3-chloropropane. 

Bromo-3-chloropropane Acetophenazine dimaleate Oxaflumazine disuccinate Perphenazine Reproterol... 

This or the reverse order will give the observed product (135). Alkylation of piperazine 136 with 1-bromo-3-chloropropane gives the piperazine derivative 137 use of that intermediate to alkylate heterocycle... 

Dithiaspiro[3.5]nonane, from 1,3-dithiane, 1-bromo-3-chloropropane, and n-butyllithium, 51, 76... 

Predictably, 1,2,4-triazole is alkylated preferentially at the 1-position [36, 38,39]. Specific alkylation at the 4-position can be achieved by the initial reaction with dibromomethane to form the bis-triazol-l-ylmethane (see below), followed by quat-emization of the triazole system at the 4-position and subsequent C-N cleavage of the 1,1 -methylenebistriazolium salts [40]. 1,2,3-Benztriazole yields a mixture of the isomeric 1- and 2-alkylated derivatives [41]. The 1-isomer predominates, but the ratio depends on whether the reactions are conducted in the presence, or absence, of a nonpolar organic solvent (Table 5.33). Higher ratios of the 1-isomer are obtained under solidrliquid two-phase conditions. Thus, alkylation of 1,2,3-benztriazole with benzyl chloride produces an overall yield of 95% with the l- 2-isomer ratio of ca. 5.7 1 similar reactions with diphenylmethyl and triphenylmethyl chlorides gives overall yields of 95% (9 1 ratio) and 70% (100% 1-isomer), respectively [38], 6-Substituted purines are alkylated at the N9-atom and reaction with 1-bromo-3-chloropropane yields exclusively the 9-chloropropyl derivative (cf. reaction wi phenols) [42]. 

Unsubstituted azetidine is synthesized on the kilogram scale by the condensation of 1-bromo-3-chloropropane with benzhydrylamine to give 1-benzhydrylazetidine followed by hydrogenolysis and basic workup (Scheme 18) (88SC205). 

SYNTHESIS To a solution of 3.3 g of KOH pellets in 150 mL hot MeOH, there was added 10 g 2,5-dimethoxythiophenol (see recipe for 2C-T-2 for its preparation) followed by 10 g 1-bromo-3-chloropropane. The reaction was exothermic, and immediately deposited white solids of KC1. The reaction mixture was warmed for a few min on the steam bath, and then quenched in HzO. The basic reaction mixture... 

Argon. An Organic Syntheses procedure for the dialkylation of 1,3-dithiane with 1 -bromo-3-chloropropane, as a first step in the synthesis of cyclobutanone, specified that argon, if available, be used as the inert gas in preference lo nitrogen because of its greater density. ... 

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