Carbon tetrabromide → 4-(Bromomethyl)-2-fluoro-1-(methylsulfanyl)benzene

HRID 396827Notes

Reaction equation

HRID 396827 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:10]O)[CH:5]=[CH:6][C:7]=1[S:8][CH3:9].C(Br)(Br)(Br)[Br:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:13][CH2:10][C:4]1[CH:5]=[CH:6][C:7]([S:8][CH3:9])=[C:2]([F:1])[CH:3]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 22316885[3-Fluoro-4-(methylsulfanyl)phenyl]methanol

Product 1

HCID 223168194-(Bromomethyl)-2-fluoro-1-(methylsulfanyl)benzeneYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The mixture of [3-fluoro-4-(methylsulfanyl)phenyl]methanol (9.00 g, 52.26 mmol) and carbon tetrabromide (19.06 g, 57.49 mmol) in CH2Cl2 (200 mL) was added triphenylphosphine (15.08 g, 57.49 mmol) at 0° C. After 1 hour, the mixture was concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with ethyl acetate/hexane (1/10) to provide the subtitle compound (12.16 g, 94% yield) as an oil.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customThe residue was purified by flash chromatography on silica gel eluting with ethyl acetate/hexane (1/10)

Sources & evidence

ORD record
ord-110e475de26f44c3a86595f532c079ab
Source dataset
uspto-grants-2003_08
Patent number
US06608095B2

Reaction notes

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