Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](O)[CH3:9])=[CH:4][CH:3]=1.[Br:11][Si](C)(C)C>ClCCl>[Br:11][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH3:9]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
0.5 g of 1-(4-fluorophenyl)ethanol is dissolved in 20 cm3 of dichloromethane, under an inert atmosphere, at a temperature close to 20° C. 1.24 cm3 of pure bromo(trimethyl)silane are introduced in two lots to the reaction mixture. The latter is stirred at a temperature close to 20° C. for 48 h, then it is washed with a saturated aqueous solution of sodium chloride, dried over a phase separation cartridge and concentrated using a rotary evaporator under reduced pressure (5 kPa). The 700 mg of crude product obtained are purified by filtration through a silica pellet (eluent: 10% ethyl acetate/90% cyclohexane). After concentrating the fractions under reduced pressure, 439 mg of 1-(1-bromoethyl)-4-fluorobenzene are obtained in the form of a colorless thick oil.
Workup
- customclose to 20° C
- customclose to 20° C. for 48 h
- washit is washed with a saturated aqueous solution of sodium chloride
- customdried over a phase separation cartridge
- concentrationconcentrated
- customa rotary evaporator under reduced pressure (5 kPa)
Sources & evidence
- ORD record
- ord-45567561ff1c4ecf9cfba6aac71202f4
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08372864B2
Linked notes
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