4-Bromobenzoic acid → 4-Bromobenzoyl chloride

HRID 2256063Notes

Reaction equation

HRID 2256063 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>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:13])=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 114644-Bromobenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 685154-Bromobenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 4-bromobenzoic acid (5 g) and thionyl chloride (15 mL) was stirred at the room temperature for 16 hours, heated to reflux for 6 hours and then stirred at room temperature for 16 hours. At the end of this period, the reaction mixture was diluted with chloroform and evaporated. The residue was treated with toluene, evaporated and the process was repeated three times. The product was obtained as a solid (5.63 g); MS: 221; NMR: 7,5 (m, 2), 7.9-8.1 (m, 2).

Workup

  1. temperatureheated
  2. temperatureto reflux for 6 hours
  3. stirringstirred at room temperature for 16 hours
  4. customevaporated
  5. additionThe residue was treated with toluene
  6. customevaporated

Sources & evidence

ORD record
ord-a872aecaf84b4208b7d818f8296289a9
Source dataset
uspto-grants-1997_08
Patent number
US05654299

Reaction notes

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