Hydrogen Bromide → 3,5-Difluorobenzyl bromide

HRID 1595126Notes

Reaction equation

HRID 1595126 reaction equation
[BrH:1].[F:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([F:11])[CH:10]=1)[CH2:6]O>S(=O)(=O)(O)O>[F:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([F:11])[CH:10]=1)[CH2:6][Br:1]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 5227213,5-Difluorobenzyl alcohol

Product 1

HCID 5188963,5-Difluorobenzyl bromide

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A 120 ml portion of 48% hydrobromic acid was added to 120 g of 3,5-difluorobenzyl alcohol. At room temperature, 120 ml of sulfuric acid was added dropwise thereto, and the mixture after the dropwise addition was stirred for 3 hours. The reaction solution was poured onto crashed ice, extracted with 600 ml of hexane, washed with water and saturated brine in that order and then dried with anhydrous sodium sulfate. By evaporating the solvent, 176 g of 3,5-difluorobenzyl bromide was obtained.

Workup

  1. additionthe mixture after the dropwise addition
  2. additionThe reaction solution was poured
  3. extractionextracted with 600 ml of hexane
  4. washwashed with water and saturated brine in that order
  5. dry with materialdried with anhydrous sodium sulfate
  6. customBy evaporating the solvent

Sources & evidence

ORD record
ord-d4cb1baeadbb4e56bacf12f00ce26947
Source dataset
uspto-grants-2001_09
Patent number
US06287646B1

Reaction notes

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