Sodium hydride → 2-Chloromethyl-2-(2-fluoro-4-trifluoromethylphenyl)oxirane

HRID 1732151Notes

Reaction equation

[Cl:1][CH2:2][C:3]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][C:8]=1[F:17])([OH:6])[CH2:4]Cl.[H-].[Na+]>C(O)(C)(C)C>[Cl:1][CH2:2][C:3]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][C:8]=2[F:17])[CH2:4][O:6]1

Participants

Conditions

Temperature: 100 °C

Procedure

1,3-Dichloro-2-(2-fluoro-4-trifluoromethylphenyl)-2-propanol (7 g.) was added to a solution of sodium hydride (1.45 g. of 48% dispersion in oil) in tert-butyl alcohol (30 ml.) and heated at 100° C. for 1 hour. The mixture was evaporated to dryness and the residue was partitioned between ethyl acetate and water. The organic layer was separated, washed with water and dried with anhydrous magnesium sulphate, and the filtered solution was evaporated to dryness to give 2-chloromethyl-2-(2-fluoro-4-trifluoromethylphenyl)oxirane as a yellow oil.

Workup

customThe mixture was evaporated to dryness
customthe residue was partitioned between ethyl acetate and water
customThe organic layer was separated
washwashed with water
dry with materialdried with anhydrous magnesium sulphate
customthe filtered solution was evaporated to dryness

Sources & evidence

ORD record: ord-14125b150e614f768159db7134bf899e
Source dataset: uspto-grants-1986_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04625036

Reaction notes

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