4-(2-Bromoethyl)benzonitrile

To a stirred solution of 4-(2-hydroxyethyl)benzonitrile (1.0g , 6.8mmol, 1eq.) in DCM (20 mL) was added CBr4 (4.5016g, 13.6mmol, 2.0 eq) and TPP (3.835g, 13.6mmol, 2.0 eq). The resulting solution was stirred at RT for 5h. Reaction was monitored TLC. Reaction was diluted with water and extracted with EtOAc. Organic layer was dried over sodium sulfate, filtered and the filtrated concentrated. The crude compound was isolated by column chromatography to get pure 4-(2-bromoethyl)benzonitrile (1.3 g, 91percent). LC-MS (method 23): Rt = 2.01 min; m/z = 210.05 (M+HExample 8A Example 4A; 4-(2-Bromoethyl)benzonitrile 12.42 g (0.18 mol) of hydroxylamine hydrochloride are added to a solution of 29.3 g (0.14 mol) of 4-(2-bromoethyl)benzaldehyde in 112.4 ml of formic acid, and the mixture is heated under reflux for 2 hours. After slowly cooling to room temperature, 670 ml of water are added and the reaction mixture is slowly neutralized with 6 N sodium hydroxide solution while cooling. The mixture is then extracted three times with methyl tert-butyl ether. The combined organic phases are dried over magnesium sulphate and evaporated to dryness. The resulting residue is purified by flash chromatography on silica gel (mobile phase: dichloromethane). 21.3 g (0.10 mol, 74percent yield) of a yellowish solid are obtained.A solution of 29.3 g (0.14 mol) of 4-(2-bromoethyl)benzaldehyde in 112.4 ml of formic acid is mixed with 12.42 g (0.18 mol) of hydroxylamine hydrochloride and heated under reflux for 2 hours. After slow cooling to room temperature, 670 ml of water are added, and the reaction mixture is slowly neutralized with 6 N sodium hydroxide solution while cooling. The mixture is then extracted three times with methyl tert-butyl ether. The combined organic phases are dried over magnesium sulfate and concentrated. The resulting residue is purified by flash chromatography on silica gel (mobile phase: dichloromethane). 21.3 g (0.10 mol, 74percent of theory) of a yellowish solid are obtained.To a solution of

Molecular Weight:210.07
XLogP3:2.8
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:208.98401
Monoisotopic Mass:208.98401
Topological Polar Surface Area:23.8
Heavy Atom Count:11
Complexity:150
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes