Thionyl Chloride → Benzeneacetyl chloride, 4-bromo-

HRID 2255256Notes

Reaction equation

HRID 2255256 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-2b3755763735442dba719b82873e5b54
Source dataset
uspto-grants-1993_08
Patent number
US05239075

Reaction notes

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