Water → 2-Bromo-4-(3-(trifluoromethyl)phenyl)thiazole

HRID 2263297Notes

Reaction equation

[BrH:1].C(O)(=O)C.O=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=1)[CH2:8][S:9][C:10]#[N:11].O>C(O)(=O)C>[Br:1][C:10]1[S:9][CH:8]=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[N:11]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A 25% hydrogen bromide/acetic acid (35 ml) solution was added to a solution of 2-oxo-2-[3-(trifluoromethyl)phenyl]ethyl thiocyanate (3.88 g, 15.8 mmol) in acetic acid (35 ml), and the mixture was stirred at 130° C. for 2 hours and at room temperature for 1 hour. Water was poured to the reaction mixture, and the mixture was extracted with chloroform. The extract was washed with water, and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to give 2.88 g (59.1%) of the desired product as an oil.

Workup

extractionthe mixture was extracted with chloroform
washThe extract was washed with water
dry with materialdried over anhydrous magnesium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record: ord-55fbb2e366f74911bf6a9c923abcefba
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07851473B2

Reaction notes

Loading…