1-(4-Fluorophenyl)ethanol → 1-(1-Bromoethyl)-4-fluorobenzene

HRID 387656

Reaction equation

HRID 387656 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

4

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

  1. customclose to 20° C
  2. customclose to 20° C. for 48 h
  3. washit is washed with a saturated aqueous solution of sodium chloride
  4. customdried over a phase separation cartridge
  5. concentrationconcentrated
  6. 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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