Phenyltrimethylammonium bromide dibromide → 2-Bromo-1-[4-(pentafluoro-lambda6-sulfanyl)phenyl]ethanone

HRID 1523308Notes

Reaction equation

[F:1][S:2]([F:15])([F:14])([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:11])[CH3:10])=[CH:5][CH:4]=1.[Br-:16].[Br-].[Br-].C[N+](C)(C)C1C=CC=CC=1.C[N+](C1C=CC=CC=1)(C)C.C[N+](C1C=CC=CC=1)(C)C>C1COCC1>[Br:16][CH2:10][C:9]([C:6]1[CH:5]=[CH:4][C:3]([S:2]([F:12])([F:13])([F:14])([F:15])[F:1])=[CH:8][CH:7]=1)=[O:11]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1-[4-(pentafluoro-λ6-sulfanyl)phenyl]ethanone (Preparation 41, 0.6 g, 2.44 mmol) in THF (20 mL) at 0° C. was added trimethylphenylammonium tribromide (0.962 g, 2.56 mmol). After stirring for 2 hours at 0° C. the reaction was quenched with a saturated aqueous solution of sodium hydrogen carbonate. The reaction was extracted with ethyl acetate and dried over MgSO4 before concentrating in vacuo to afford the title compound that was used without further purification.

Workup

customwas quenched with a saturated aqueous solution of sodium hydrogen carbonate
extractionThe reaction was extracted with ethyl acetate
dry with materialdried over MgSO4
concentrationbefore concentrating in vacuo

Sources & evidence

ORD record: ord-521fbeb30fb5407586e28e235ed7b868
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079878B2

Reaction notes

Loading…