Water → 1-[5-Bromo-4-(cyclopropylmethoxy)-2-methylphenyl]ethanone

HRID 2093829Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

A suspension of 1-(4-cyclopropylmethoxy-2-methyl-phenyl)-ethanone from example A24 (6.4 g, 31.3 mmol) and N-bromosuccinimide (6.20 g, 34.5 mmol) in dry dimethylformamide (50 mL) is heated for 3 h at 50° C. After cooling to ambient temperature, water (200 mL) is added and the mixture is extracted with ethyl acetate (3×60 mL). The combined organic extracts are dried over sodium sulfate. The solvent is removed under reduced pressure. The crude is purified by column chromatography on silica gel using dichloromethane as eluent to give the title compound as a off-white solid. Yield: 4.80 g.

Workup

temperatureAfter cooling to ambient temperature
extractionthe mixture is extracted with ethyl acetate (3×60 mL)
dry with materialThe combined organic extracts are dried over sodium sulfate
customThe solvent is removed under reduced pressure
customThe crude is purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-46b9f39875d14c658a738fc7e29e52f6
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445501B2

Reaction notes

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