Water → 1-Bromo-3-cyclopropylthiobenzene

HRID 70580

Reaction equation

[CH3:1][C:2]([CH3:5])([O-])C.[K+].C1(Br)CC1.[Br:11][C:12]1[CH:13]=[C:14]([SH:18])[CH:15]=[CH:16][CH:17]=1.O>CS(C)=O>[Br:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([S:18][CH:5]2[CH2:2][CH2:1]2)[CH:13]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Potassium t-butoxide (4 g) and cyclopropyl bromide (7.6 mL) were added to a solution of 3-bromothiophenol (6 g) in dimethyl sulfoxide (30 mL), and the mixture was stirred at 80° C. for five hours. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was sequentially washed with water and brine, dried over sodium sulfate and filtered, after which the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→7:3) to give the title compound as a light yellow oil (1.6 g, 23%).

Workup

extractionfollowed by extraction with ethyl acetate
washThe organic layer was sequentially washed with water and brine
dry with materialdried over sodium sulfate
filtrationfiltered
customafter which the solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→7:3)

Sources & evidence

ORD record: ord-a19d8c44d44b4ffb8dec7cb54f0906e5
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822503B2

Linked notes

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