p-Toluenesulfonic acid → 2,2-Dimethyl-3-[2-trifluoromethyl-2-bromo-2-chloro-1-methylsulfonylethyl]-cyclopropane carboxylic acid

HRID 5641Notes

Reaction equation

HRID 5641 reaction equation
C1(C)C=C[C:4]([S:7](O)(=[O:9])=[O:8])=CC=1.[CH3:12][C:13]1([CH3:32])[CH:15]([CH:16](OS(C)(=O)=O)[C:17]([C:20]([F:23])([F:22])[F:21])([Br:19])[Cl:18])[CH:14]1[C:29]([O-:31])=[O:30]>C(Cl)Cl>[CH3:32][C:13]1([CH3:12])[CH:15]([CH:16]([S:7]([CH3:4])(=[O:9])=[O:8])[C:17]([C:20]([F:21])([F:22])[F:23])([Br:19])[Cl:18])[CH:14]1[C:29]([OH:31])=[O:30]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 197968822,2-Dimethyl-3-[2-trifluoromethyl-2-bromo-2-chloro-1-methylsulfonyloxyethyl]-cyclopropane carboxylate

Product 1

HCID 197969102,2-Dimethyl-3-[2-trifluoromethyl-2-bromo-2-chloro-1-methylsulfonylethyl]-cyclopropane carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

30 mg of p-toluene sulfonic acid were added at 40° C. to a solution of 1 g of the product of Step B and 10 ml of methylene chloride and the reaction mixture was heated for 5 hours at 40° C., then poured on to ice, and decanted. The organic phase was washed with water, dried on sodium sulfate and evaporated to dryness under reduced pressure to obtain 860 mg of [1R-[1α-,3α-(RS*,RS*)]] 2,2-dimethyl-3-[2-trifluoromethyl-2-bromo-2-chloro-1-methylsulfonylethyl]-cyclopropane carboxylic acid melting at 138° C.

Workup

  1. additionpoured on to ice
  2. customdecanted
  3. washThe organic phase was washed with water
  4. customdried on sodium sulfate
  5. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-fdacc60898794503bab31670ff34e1da
Source dataset
uspto-grants-1993_09
Patent number
US05245073

Reaction notes

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