Dimethylformamide → (2,3,5,6-tetrafluoro-4-methylphenyl)methyl(1RS)-trans-2,2-dimethyl-3-((E)-1-propenyl)cyclopropanecarboxylate

HRID 1976311Notes

Reaction equation

[CH3:1][C:2]1([CH3:11])[C@@H:4](/[CH:5]=[CH:6]/[CH3:7])[C@@H:3]1[C:8]([OH:10])=[O:9].Br[CH2:13][C:14]1[C:19]([F:20])=[C:18]([F:21])[C:17]([CH3:22])=[C:16]([F:23])[C:15]=1[F:24].CN(C)C=O.C(N(CC)CC)C>O>[CH3:11][C:2]1([CH3:1])[C@@H:4](/[CH:5]=[CH:6]/[CH3:7])[C@@H:3]1[C:8]([O:10][CH2:13][C:14]1[C:15]([F:24])=[C:16]([F:23])[C:17]([CH3:22])=[C:18]([F:21])[C:19]=1[F:20])=[O:9]

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture solution of 0.50 g of (1RS)-trans-2,2-dimethyl-3-((E)-1-propenyl)cyclopropanecarboxylic acid, 0.72 g of 1-bromomethyl-2,3,5,6-tetrafluoro-4-methylbenzene and 8 ml of dimethylformamide, 1.0 g of triethylamine was added and the mixture was stirred at 80° C. for 4 hours. After the mixture was cooled to room temperature, water was poured into the mixture and the mixture was extracted with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (eluent: hexane/ethyl acetate=20/1) to give 0.83 g of (2,3,5,6-tetrafluoro-4-methylphenyl)methyl(1RS)-trans-2,2-dimethyl-3-((E)-1-propenyl)cyclopropanecarboxylate

Workup

temperatureAfter the mixture was cooled to room temperature
extractionthe mixture was extracted with diethyl ether
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-024bda9c046d4a68a0512bd78260a400
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06225495B1

Reaction notes

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