4-Bromobenzoic acid → 4-Bromobenzoyl chloride

HRID 1604126Notes

Reaction equation

HRID 1604126 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][CH:3]=1.S(Cl)([Cl:13])=O>C(Cl)(Cl)Cl.CN(C)C=O>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:13])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 114644-Bromobenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 685154-Bromobenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6212ChloroformSolvent2×

Procedure

A round bottom flask was charged with 4-bromobenzoic acid (2.0 g, 9.95 mmol) in chloroform (150 mL). To the solution was added thionyl chloride (3 mL) in chloroform (10 mL), 2-3 drops of dimethylformamide (DMF). The slurry was heated at reflux for 3 hr. while monitoring the reaction through a bubbler. A clear solution of 4-bromobenzoyl chloride was obtained, the volatiles were removed and a light yellow oil was obtained which solidified upon cooling.

Workup

  1. temperatureThe slurry was heated
  2. temperatureat reflux for 3 hr
  3. customthe reaction through a bubbler

Sources & evidence

ORD record
ord-c10e1b4ef52445e08454c07498a2ada8
Source dataset
uspto-grants-1999_11
Patent number
US05993777

Reaction notes

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