Dimethylformamide → 4-Bromo-2-chlorobenzoyl chloride

HRID 963423Notes

Reaction equation

HRID 963423 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([Cl:11])[CH:3]=1.CN(C)C=O.S(Cl)([Cl:19])=O>CCCCCC>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:19])=[O:7])=[C:4]([Cl:11])[CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 1088294-Bromo-2-chlorobenzoic acid

Product 1

HCID 155922074-Bromo-2-chlorobenzoyl chlorideYield 99%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

13bk) 49.4 g of 4-bromo-2-chloro-benzoic acid were suspended in 60 ml of hexane, treated with 0.2 ml of N,N-dimethylformamide and 18.5 ml of thionyl chloride and boiled at reflux under argon for 15 hrs. The resulting solution was cooled to room temperature, filtered, evaporated and the residue was again evaporated with 60 ml of toluene. There were obtained 53 g (99%) of 4-bromo-2-chloro-benzoylchloride as a crude oil which crystallized upon standing, but which was used directly in the next step without further manipulation.

Workup

  1. temperatureat reflux under argon for 15 hrs
  2. filtrationfiltered
  3. customevaporated
  4. customthe residue was again evaporated with 60 ml of toluene

Sources & evidence

ORD record
ord-806b4b1f329d42eda520b3c0be52e724
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Reaction notes

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