Imidazole → HCID 12848950, compound

HRID 2296333Notes

Reaction equation

[F:1][CH2:2][C:3]([CH2:20][F:21])([CH3:19])[C:4](=[O:18])[CH:5](Br)[O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=1.[NH:22]1[CH:26]=[CH:25][N:24]=[CH:23]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[F:1][CH2:2][C:3]([CH2:20][F:21])([CH3:19])[C:4](=[O:18])[CH:5]([N:22]1[CH:26]=[CH:25][N:24]=[CH:23]1)[O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=1

Participants

Conditions

Temperature: 50 °C

Procedure

135 g (0.36 mole) of 3,3-bisfluoromethyl-1-bromo-1-(3-trifluoromethyl-phenoxy)-butan-2-one in 400 ml of acetone were added dropwise to 24.5 g (0.36 mole) of imidazole and 55.3 g (0.4 mole) of potassium carbonate in 400 ml of acetone. The mixture was stirred at 50° C. for 6 hours and was then concentrated by distilling off the solvent under a waterpump vacuum. The oily residue was taken up in 800 ml of methylene chloride, the mixture was washed twice with 2,000 ml of water each time, the organic phase was stirred with active charcoal, filtered and dried over sodium sulphate and the solvent was distilled off. The oily residue was distilled under a high vacuum. 63.4 g (48.8% of theory) of 3,3-bisfluoromethyl-1-(imidazol-1-yl)-1-(3-trifluoromethyl-phenoxy)-butan-2-one of boiling point 169°-73° C./0.1 mm Hg were obtained.

Workup

concentrationwas then concentrated
distillationby distilling off the solvent under a waterpump vacuum
washthe mixture was washed twice with 2,000 ml of water each time
stirringthe organic phase was stirred with active charcoal
filtrationfiltered
dry with materialdried over sodium sulphate
distillationthe solvent was distilled off
distillationThe oily residue was distilled under a high vacuum

Sources & evidence

ORD record: ord-7c0eb971e88b46ac8fc9089dd7ebe0d5
Source dataset: uspto-grants-1984_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04428949

Reaction notes

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