Oxalyl chloride → (+)-cis-3-(2,2-Dibromoethenyl)-2,2-dimethylcyclopropanecarbonyl chloride

HRID 905380Notes

Reaction equation

HRID 905380 reaction equation
[Br:1][C:2]([Br:12])=[CH:3][C@@H:4]1[C@H:6]([C:7](O)=[O:8])[C:5]1([CH3:11])[CH3:10].C(Cl)(=O)C([Cl:16])=O>C1(C)C=CC=CC=1>[Br:1][C:2]([Br:12])=[CH:3][C@@H:4]1[C@H:6]([C:7]([Cl:16])=[O:8])[C:5]1([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 12525241cis-3-(2,2-Dibromovinyl)-2,2-dimethylcyclopropane-1-carboxylic acid

Product 1

HCID 86738410(+)-cis-3-(2,2-Dibromoethenyl)-2,2-dimethylcyclopropanecarbonyl chlorideYield 50.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a manner similar to Example 13A, the reaction of 13.0 g (0.0436 mole) of (+)-cis-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylic acid, 50 ml of toluene, and 11.1 g (0.0873 mole) of oxalyl chloride gave 7.0 g of (+)-cis-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarbonyl chloride. The nmr spectrum was consistent with the proposed structure.

Sources & evidence

ORD record
ord-92e57a4419f7452883825be55c34b16b
Source dataset
uspto-grants-1983_12
Patent number
US04423255

Reaction notes

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