Phosphorus tribromide → 4-(Bromomethyl)-2-chloro-1-fluorobenzene

HRID 2277592Notes

Reaction equation

HRID 2277592 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9]O)[CH:5]=[CH:6][C:7]=1[F:8].P(Br)(Br)[Br:12]>C(Cl)Cl>[Br:12][CH2:9][C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Cl:1])[CH:3]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 27736073-Chloro-4-fluorobenzyl alcohol

Product 1

HCID 27575424-(Bromomethyl)-2-chloro-1-fluorobenzeneYield 61.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-chloro-4-fluoro-phenyl)-methanol (4.3 g, 26.8 mmol) in DCM (20 mL) was added PBr3 (1 mL) at 0° C. The resulting mixture was stirred at room temperature for 1 hour before it was quenched with satd. aq. NaHCO3 solution. The organic solution was washed with water, brine, dried over anhy. Na2SO4 and concentrated in vacuo to give the desired product (3.7 g, 61.9%). It was used directly in the next step, without further purification.

Workup

  1. customwas quenched with satd
  2. washThe organic solution was washed with water, brine
  3. customdried over anhy
  4. concentrationNa2SO4 and concentrated in vacuo

Sources & evidence

ORD record
ord-7deaae9262754026a7cb9a1d5e7f5af4
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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