Thionyl Chloride → (RS)-2-bromo-2-(3-chlorophenyl)acetyl chloride

Reaction equation

[Br:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8](Br)[CH:7]=1)[C:3]([Cl:5])=[O:4].BrC(C1C=CC(Cl)=CC=1)C([Cl:17])=O.BrC1C=C(CC(O)=O)C=CC=1.S(Cl)(Cl)=O.BrBr>>[Br:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:17])[CH:7]=1)[C:3]([Cl:5])=[O:4]

Participants

Reactant 5

HCID 24386Thionyl Chloride

HCID 24408Bromine

HCID 74653(3-Bromophenyl)acetic acid

HCID 12575778Bromo-4-chlorophenylacetyl chloride

HCID 189511352-Bromo-2-(3-bromophenyl)acetyl chloride

Product 1

HCID 18951149(RS)-2-bromo-2-(3-chlorophenyl)acetyl chloride

Procedure

(RS)-2-Bromo-2-(3-bromophenyl)acetyl chloride may be prepared by the method described in Example 9 for the preparation of (RS)-2-bromo-2-(4-chlorophenyl)acetyl chloride, but using 5 g of 2-(3-bromophenyl)acetic acid, 2.8 cm3 of thionyl chloride and 1.5 cm3 of bromine as starting materials. 7 g of (RS)-2-bromo-2-(3-chlorophenyl)acetyl chloride are then obtained, which is used as such for the following step.