3-Chlorobenzoic Acid → 2-Bromo-1-(4-chlorophenyl)propan-1-one

HRID 894270Notes

Reaction equation

HRID 894270 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:11])[CH2:9][CH3:10])=[CH:4][CH:3]=1.ClCCl.ClC1C=C(C=CC=1)C(O)=O.[Br:25]Br>CC(C)=O>[Br:25][CH:9]([CH3:10])[C:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)=[O:11]

Participants

6

Reactant 4

HCID 4473-Chlorobenzoic AcidHCID 6344Dichloromethane2×HCID 226974'-ChloropropiophenoneHCID 24408Bromine

Product 1

HCID 37882192-Bromo-1-(4-chlorophenyl)propan-1-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A 6.6 g. portion of p-chloropropiophenone is dissolved in 150 ml. of dichloromethane and 100 mg. of m-chlorobenzoic acid are added. The solution is stirred as a mixture of 6.0 g. of bromine in 50 ml. of dichloromethane is added dropwise. The solution is stirred for 2 hours, taken to dryness in vacuo and the oil is dissolved in 100 ml. of acetone and clarified, providing an acetone solution of 2-bromo-4'-chloropropiophenone. A 50 ml. portion of this acetone solution is added to a stirred solution of 3.0 g. of hexahydro-1,3-diazocine-2(1H)-thione in 500 ml. of acetone. The mixture is stirred for 18 hours, the solid is collected, washed with 100 ml. of acetone and dried in vacuo, giving 1.6 g. of the desired product, m.p. 212°-213° C. (dec.).

Workup

  1. stirringThe solution is stirred for 2 hours
  2. dissolutionthe oil is dissolved in 100 ml

Sources & evidence

ORD record
ord-8269dfe2ea35472d81e3492ba363123f
Source dataset
uspto-grants-1981_08
Patent number
US04283334

Reaction notes

Loading…