Thionyl Chloride → a-(3-Bromopropyl)-4-fluoro-alpha-(4-fluorophenyl)benzeneacetyl chloride

HRID 35310Notes

Reaction equation

HRID 35310 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][C:5]([C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)[C:6](O)=[O:7].S(Cl)([Cl:25])=O>ClC(Cl)Cl>[Br:1][CH2:2][CH2:3][CH2:4][C:5]([C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)[C:6]([Cl:25])=[O:7]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 14230261HCID 14230261, compound

Product 1

HCID 19883439a-(3-Bromopropyl)-4-fluoro-alpha-(4-fluorophenyl)benzeneacetyl chloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of 29.5 parts of α-(3-bromopropyl)-4-fluoro-α-(4-fluorophenyl)benzeneacetic acid in 300 parts of trichloromethane were added 28.8 parts of thionyl chloride and the whole was stirred and refluxed for 3 hours. The reaction mixture was evaporated, yielding 30 parts of α-(3-bromopropyl)-4-fluoro-α-(4-fluorophenyl)benzeneacetyl chloride as a residue (intermediate 17).

Workup

  1. temperaturerefluxed for 3 hours
  2. customThe reaction mixture was evaporated

Sources & evidence

ORD record
ord-903620fc72a54bdfabd4115c32e0254c
Source dataset
uspto-grants-1988_08
Patent number
US04766125

Reaction notes

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