1-(2-Bromoethyl)-3-chlorobenzene

Add triphenylphoshpine (3.90 g, 14.9 mmol) to a stirred solution of 3- chlorophenethyl alcohol (2.0 mL, 14.8 mmol), carbon tetrabromide (4.91 g, 14.8 mmol) and anhydrous dichloromethane (100 mL). Stir for 5 h under nitrogen at room temperature, and then wash with water (100 mL) and brine (100 mL). Dry the dichloromethane layer over magnesium sulfate, filter, and concentrate on a rotary evaporator to give the crude product. The crude product is purified by flash chromatography on silica gel eluting with 100percent hexanes to yield 2. 30 g (71percent) of 1- (2- bromo-ethyl) -3-chloro-benzene: TLC: Rf in 100percent hexanes : 0.27 ; LH NMR (CDC13) : 7.26-7. 11 (m, 3H), 7.09-7. 07 (m, 1H), 3.54 (t, 2H), 3.12 (t, 2H).Specific operations are as follows: 20g of m-chlorophenylacetic acid was added to 200ml of tetrahydrofuran, cooled to 0 ° C with stirring, At the beginning of batch addition of 8.9g of lithium aluminum hydride, the temperature was raised to 25 ~ 30 after the addition, the reaction 4h after the addition of water 300ml, dichloromethane400 ml of the mixture was separated, and the organic phase was added with 20 g of anhydrous sodium sulfate and dried under reduced pressure at 30-35 ° C. to obtain a pale yellow oil (S1-1): 18.3 g; Dropping phosphorus tribromide, the dropping temperature during the control at 0 ~ 10 ° C, dropping completed, After stirring for 10min, the temperature was raised to 75-80 ° C, After stirring for 2h, 30ml of saturated sodium bicarbonate solution, 200ml of ethyl acetate, The mixture was stirred for 20 minutes, and the filtrate was concentrated under reduced pressure at 40-45 ° C. to give a yellow liquid (intermediate S2): 22.4 g. Yield: 87.0percent.To a solution of 2- (3-chlorophenyl) ethanol (1.06 g, 6.0 mmol) in CH2CL2 (50 mL) at RT under nitrogen was added CBr4 (1.98 g, 5.8 mmol) and PPh3 (1.57 g, 5.8 mmol). After stirring at RT for 18 h the reaction mixture was concentrated and the residue diluted with ETZO (30 mL) resulting in precipitation of triphenylphosphine oxide. The ethereal solution was decanted, evaporated and purified via flash chromatography (silica, hexane) to provide 2- (3-CHLORO) phenylethyl bromide as a clear oil (57percent). 1H NMR (400 MHz, DMSO-d6) 8 7.39-7. 22 (m, 3 H), 7.18-7. 09 (m, 1 H), 3.63-3. 51 (m, 2 H), 3.25-3. 17 (m, 2 H); 13C NMR (100.6 MHz, DMSO-d6) B 141.2, 134.6, 130.7, 129.3, 127.6, 127.3.

Molecular Weight:219.50
XLogP3:3.9
Rotatable Bond Count:2
Exact Mass:217.94979
Monoisotopic Mass:217.94979
Heavy Atom Count:10
Complexity:95.3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes