Thionyl Chloride → Benzeneacetyl chloride, 4-bromo-

HRID 1683882Notes

Reaction equation

HRID 1683882 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.S(Cl)([Cl:14])=O>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([Cl:14])=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 74654Benzeneacetic acid, 4-bromo-

Product 1

HCID 181552Benzeneacetyl chloride, 4-bromo-Yield 73.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-bromo-phenyl acetic acid (25 g, 116 mmol) in dichloromethane (250 ml) was added thionyl chloride (13 ml, 170 mmol). The mixture was heated under reflux for 24 hours and then the solvent and the excess reagent were removed. The residue was distilled under reduced pressure (110° C./2 mmHg) to yield 19.8 g (73%) of the title compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 24 hours
  3. customthe solvent and the excess reagent were removed
  4. distillationThe residue was distilled under reduced pressure (110° C./2 mmHg)

Sources & evidence

ORD record
ord-bb1f3b799aee4c2185d7dc358710ef8d
Source dataset
uspto-grants-1997_06
Patent number
US05639778

Reaction notes

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