Water → 3-Bromo-4-fluorobenzyl Bromide

HRID 2286048Notes

Reaction equation

HRID 2286048 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH2:5]O.P(Br)(Br)[Br:12].O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH2:5][Br:12]

Participants

5

Reactant 3

HCID 962WaterHCID 24614Phosphorus tribromideHCID 27733513-Bromo-4-fluorobenzyl Alcohol

Product 1

HCID 129227103-Bromo-4-fluorobenzyl BromideYield 242.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

20.5 g (0.1 mol) of 3-bromo-4-fluoro-benzyl alcohol were dissolved in 100 ml of anhydrous toluene, and 10 g of phosphorus tribromide were added dropwise at 0° to 10° C., while stirring. The mixture was then stirred at room temperature for 2 hours. The reaction batch was subsequently poured into 500 ml of water, the organic phase was separated off and dried over magnesium sulphate and the solvent was distilled off under a waterpump vacuum. The residue was distilled in vacuo. 24 g (89.6% of theory) of 3-bromo-4-fluoro-benzyl bromide with a boiling point of 99°-100° C./3 mbars were obtained.

Workup

  1. stirringThe mixture was then stirred at room temperature for 2 hours
  2. customthe organic phase was separated off
  3. dry with materialdried over magnesium sulphate
  4. distillationthe solvent was distilled off under a waterpump vacuum
  5. distillationThe residue was distilled in vacuo

Sources & evidence

ORD record
ord-f1520009c92d4191b142acc85da6f066
Source dataset
uspto-grants-1982_04
Patent number
US04326087

Reaction notes

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