Thionyl Chloride → (S)alpha-cyano-3-phenoxy-4-fluorobenzyl (1R,cis,Z) 2,2-dimethyl-3-[3-oxo-3-chloro-1-propenyl]-cyclopropane-carboxylate

HRID 1639460Notes

Reaction equation

HRID 1639460 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][C:6]1([CH3:34])[C@@H:8](/[CH:9]=[CH:10]\[C:11](=O)[OH:12])[C@H:7]1[C:14]([O:16][C@H:17]([C:32]#[N:33])[C:18]1[CH:23]=[CH:22][C:21]([F:24])=[C:20]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:19]=1)=[O:15]>C(Cl)Cl>[CH3:5][C:6]1([CH3:34])[C@@H:8](/[CH:9]=[CH:10]\[C:11](=[O:12])[Cl:3])[C@H:7]1[C:14]([O:16][C@H:17]([C:32]#[N:33])[C:18]1[CH:23]=[CH:22][C:21]([F:24])=[C:20]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:19]=1)=[O:15]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 86740328(S)alpha-cyano-3-phenoxy-4-fluoro-benzyl(1R,cis,Z)2,2-dimethyl-3-[3-oxo-3-hydroxy-1-propenyl]-cyclopropane-carboxylate

Product 1

HCID 86740334(S)alpha-cyano-3-phenoxy-4-fluorobenzyl (1R,cis,Z) 2,2-dimethyl-3-[3-oxo-3-chloro-1-propenyl]-cyclopropane-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10 ml of thionyl chloride were added all at once at 20° C. to a solution of 4.5 g of the product of Step C in 20 ml of methylene chloride and the mixture was stirred for 105 minutes and was evaporated to dryness under reduced pressure to obtain 4.7 g of (S)α-cyano-3-phenoxy-4-fluorobenzyl (1R,cis,Z) 2,2-dimethyl-3-[3-oxo-3-chloro-1-propenyl]-cyclopropane-carboxylate.

Workup

  1. customwas evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-f41feead44814a928d91df96ae415f99
Source dataset
uspto-grants-1989_11
Patent number
US04883806

Reaction notes

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