Thionyl Chloride → Benzeneacetyl chloride, 4-bromo-

HRID 1386490Notes

Reaction equation

HRID 1386490 reaction equation
S(Cl)([Cl:3])=O.[Br:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([OH:15])=O)=[CH:8][CH:7]=1>C1(C)C=CC=CC=1>[Br:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([Cl:3])=[O:15])=[CH:8][CH:7]=1

Participants

4

Reactant 2

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

Product 1

HCID 181552Benzeneacetyl chloride, 4-bromo-Yield 102.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Thionyl chloride (2.5 ml, 34.8 mmol) is added at ambient temperature to a solution of 4-bromophenylacetic acid (Aldrich, 5 g, 23.2 mmol) in 10 ml of toluene. The reaction medium is brought to reflux for 2 hours. After returning to ambient temperature, the toluene is evaporated and 5.55 g of raw 4-bromophenylacetyl chloride is obtained (gross yield=100%).

Workup

  1. temperatureto reflux for 2 hours
  2. customAfter returning to ambient temperature
  3. customthe toluene is evaporated

Sources & evidence

ORD record
ord-5d443b11111c4e18a28fb6081c411940
Source dataset
uspto-grants-2001_07
Patent number
US06265423B1

Reaction notes

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