Phosphorus tribromide → 1-(Bromomethyl)-3-chloro-2-fluorobenzene

HRID 2277576Notes

Reaction equation

HRID 2277576 reaction equation
[Cl:1][C:2]1[C:3]([F:10])=[C:4]([CH2:8]O)[CH:5]=[CH:6][CH:7]=1.P(Br)(Br)[Br:12]>C(Cl)Cl>[Br:12][CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[F:10]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 27736063-Chloro-2-fluorobenzyl alcohol

Product 1

HCID 5228271-(Bromomethyl)-3-chloro-2-fluorobenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-chloro-2-fluoro-phenyl)-methanol (3.2 g, 20 mmol) in DCM (20 mL) was added dropwise PBr3 (1 mL) at 0° C. The reaction mixture was stirred at room temperature for another 1 hour before quenching with satd. aq. NaHCO3 solution. The organic layer was washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give the desired product without further purification (4.1 g, 92%). MS: 223.2 (M+H)+.

Workup

  1. custombefore quenching with satd
  2. washThe organic layer was washed with brine
  3. customdried over anhy
  4. filtrationNa2SO4, filtered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-83f5b1b3b60342609dee565456a80b17
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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