Carbon tetrabromide → 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 100% hexanes to yield 2.30 g (71%) of 1-(2-bromo-ethyl)-3-chloro-benzene: TLC: Rf in 100% hexanes: 0.27; 1H NMR (CDCl3): 7.26-7.11 (m, 3H), 7.09-7.07 (m, 1H), 3.54 (t, 2H), 3.12 (t, 2H).

1. washwash with water (100 mL) and brine (100 mL)
2. dry with materialDry the dichloromethane layer over magnesium sulfate
3. filtrationfilter
4. concentrationconcentrate on a rotary evaporator
5. customto give the crude product
6. customThe crude product is purified by flash chromatography on silica gel eluting with 100% hexanes

ORD record

ord-ae5d56f43ca84e96ae4787c32da53888

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07560463B2