Thionyl Chloride → Benzeneacetyl chloride, 4-bromo-

HRID 1379061Notes

Reaction equation

HRID 1379061 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>>[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

3

Reactant 2

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

Product 1

HCID 181552Benzeneacetyl chloride, 4-bromo-Yield 99.9%

Procedure

To a 250 ml round bottom flask fitted with a magnetic stirrer was added 4-bromophenylacetic acid (100.0 g; 0.465 mol) and 100 ml of thionyl chloride (163.1 g; 1.37 mol). The resulting slurry was stirred at room temperature for 22.5 hrs. The excess thionyl chloride was evaporated under vacuum to afford 108.5 g of the subtitle compound as a brown liquid.

Workup

  1. customTo a 250 ml round bottom flask fitted with a magnetic stirrer
  2. customThe excess thionyl chloride was evaporated under vacuum

Sources & evidence

ORD record
ord-8630dce71cea4fc9aba54a4667239ca7
Source dataset
uspto-grants-1997_09
Patent number
US05670512

Reaction notes

Loading…