Phosphorus tribromide → 2-Chloro-5-fluorobenzyl bromide

HRID 240287Notes

Reaction equation

HRID 240287 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH2:9]O.P(Br)(Br)[Br:12]>COCCOC.O>[Br:12][CH2:9][C:3]1[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 2773605(2-Chloro-5-fluorophenyl)methanol

Product 1

HCID 27736232-Chloro-5-fluorobenzyl bromide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a solution of (2-chloro-5-fluorophenyl)methanol (24, 25.5 g, 159 mmol) in dry DME (200 mL) at 0° C. was added a solution of PBr3 (25.8 g, 95.2 mmol) in dry DME (150 mL) dropwise. The mixture was then slowly warmed up to RT and stirred at RT for another 3 h. The mixture was diluted with water (300 mL), and extracted with 1:1 petroleum-ether-EtOAc (200 mL×2). The combined extracts were washed with saturated NaHCO3 and brine, dried over MgSO4, and concentrated to give 2-(bromomethyl)-1-chloro-4-fluorobenzene (25).

Workup

  1. extractionextracted with 1:1 petroleum-ether-EtOAc (200 mL×2)
  2. washThe combined extracts were washed with saturated NaHCO3 and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-dffacd4a0aba4fadb968c45323cf08c4
Source dataset
uspto-grants-2014_02
Patent number
US08648073B2

Reaction notes

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