Thionyl Chloride → 2-Bromo-4-(chloromethyl)-1-fluorobenzene

HRID 1702509Notes

Reaction equation

HRID 1702509 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH2:5]O.S(Cl)([Cl:13])=O>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH2:5][Cl:13]

Participants

4

Reactant 2

HCID 24386Thionyl Chloride2×HCID 27733513-Bromo-4-fluorobenzyl Alcohol

Product 1

HCID 129227112-Bromo-4-(chloromethyl)-1-fluorobenzeneYield 64.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

41 g (0.2 mol) of 3-bromo-4-fluoro-benzyl alcohol were dissolved in 250 ml of carbon tetrachloride, and 26 g of thionyl chloride were added dropwise at 20° C., while stirring. The mixture was then stirred at 25°-30° C. for 4 hours and the solvent and excess thionyl chloride were subsequently stripped off at 20° C. under a waterpump vacuum. The residue was distilled in vacuo. 29 g (64.9% of theory) of 3-bromo-4-fluoro-benzyl chloride with a boiling point of 85°-87° C./3 mbars were obtained.

Workup

  1. stirringThe mixture was then stirred at 25°-30° C. for 4 hours
  2. customwere subsequently stripped off at 20° C. under a waterpump vacuum
  3. distillationThe residue was distilled in vacuo

Sources & evidence

ORD record
ord-cfd9e19c37084243890a47dc3fde0923
Source dataset
uspto-grants-1983_04
Patent number
US04381412

Reaction notes

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