N-bromobutanimide → (R)-2-[2-(2-bromomethylphenyl)-2-methylpropyl]-2-trifluoromethyloxirane

HRID 2387323Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([CH3:18])([CH3:17])[CH2:9][C@:10]1([C:13]([F:16])([F:15])[F:14])[CH2:12][O:11]1.[Br:19]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:19][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([CH3:18])([CH3:17])[CH2:9][C@:10]1([C:13]([F:14])([F:16])[F:15])[CH2:12][O:11]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirred solution of (R)-2-[2-(2-methylphenyl)-2-methylpropyl]-2-trifluoromethyloxirane (37 g, 0.143 mmol) in 500 mL of anhydrous CCl4 at room temperature was added N-bromosuccinimide (26 g, 0.146 mmol). The reaction mixture was heated to 70° C. and the reaction flask was irradiated with a UV light (500 W) for 1 hour. The reaction mixture, after cooling to normal room temperature, was washed with saturated aqueous sodium bicarbonate solution followed by water, dried over anhydrous sodium sulfate, and the solvent evaporated in vacuo to give (R)-2-[2-(2-bromomethylphenyl)-2-methylpropyl]-2-trifluoromethyloxirane as a light yellow oil (46.6 g, 81%; ˜85% pure) which was used for the next reaction without purification.

Workup

customthe reaction flask was irradiated with a UV light (500 W) for 1 hour
temperatureThe reaction mixture, after cooling to normal room temperature
washwas washed with saturated aqueous sodium bicarbonate solution
dry with materialdried over anhydrous sodium sulfate
customthe solvent evaporated in vacuo

Sources & evidence

ORD record: ord-0df0a3ab672849fb842c4a85fe7a11f6
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268859B2

Reaction notes

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