Acetonitrile → 3,3-Bis-fluoromethyl-1-(4-chlorophenoxy)-1-(1,2,4-triazol-4-yl)-butan-2-one

HRID 851130Notes

Reaction equation

[F:1][CH2:2][C:3]([CH2:17][F:18])([CH3:16])[C:4](=[O:15])[CH:5](Br)[O:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1.N1C=[CH:22][N:21]=[N:20]1.[C:24](#[N:26])C>C(Cl)Cl>[F:1][CH2:2][C:3]([CH2:17][F:18])([CH3:16])[C:4](=[O:15])[CH:5]([O:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)[N:26]1[CH:22]=[N:21][N:20]=[CH:24]1

Participants

Conditions

Temperature: 50 °C

Procedure

82 g (0.286 mol) of 3,3-bis-fluoromethyl-1-bromo-1-(4-chlorophenoxy)-butan-2-one and 41.5 g (0.588 mol) of triazole were introduced into 600 ml of acetonitrile, the mixture was heated at 50° C. for 5 hours, the solvent was driven off under a waterpump vacuum, the residue was taken up in one liter of methylene chloride, the methylene chloride mixture was washed twice with 1,000 ml of water each time, the organic phase was dried over sodium sulphate and the solvent was distilled off. The residue was taken up in 500 ml of diisopropyl ether and the precipitate was filtered off. 6 g of 3,3-bis-fluoromethyl-1-(4-chlorophenoxy)-1-(1,2,4-triazol-4-yl)-butan-2-one (compound 3) of melting point 119°-122° C. were obtained. The mother liquor was distilled. 32.1 g (40% of theory) of 3,3-bis-fluoromethyl-1-(4-chlorophenoxy)-1-(1,2,4-triazol-1-yl)-butan-2-one (compound 4) of boiling point 160° -166° C./0.2 mm Hg were obtained.

Workup

washthe methylene chloride mixture was washed twice with 1,000 ml of water each time
dry with materialthe organic phase was dried over sodium sulphate
distillationthe solvent was distilled off
filtrationthe precipitate was filtered off

Sources & evidence

ORD record: ord-f91518ddb2ce44d8afca79ceb6fe5f46
Source dataset: uspto-grants-1983_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04382944

Reaction notes

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