Bromine → 5-Bromo-2-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3-thiazole

HRID 1942639Notes

Reaction equation

[CH3:1][CH:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:12][CH:13]=[CH:14][N:15]=2)=[CH:7][C:6]=1[C:16]([F:19])([F:18])[F:17])[CH3:3].C([O-])(=O)C.[Na+].[Br:25]Br>C(O)(=O)C>[Br:25][C:13]1[S:12][C:11]([C:8]2[CH:9]=[CH:10][C:5]([O:4][CH:2]([CH3:1])[CH3:3])=[C:6]([C:16]([F:19])([F:17])[F:18])[CH:7]=2)=[N:15][CH:14]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of 2-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3-thiazole (D66) (143 mg) and sodium acetate (82 mg) in acetic acid (5 mL) stirred at 5° C. was added a solution of Br2 (0.026 mL) in acetic acid (1 mL) dropwise. The reaction mixture was stirred at 20° C. until start material was consumed completely. The reaction mixture was basified with 2M NaOH. The resulting solution was diluted with ethyl acetate. The mixture was washed with brine. The organic phase was dried over anhydrous sodium sulphate and evaporated in vacuo. The crude product was purified by column chromatography to give 5-bromo-2-[4-[(1-methylethyl)oxy]-3-(trifluoromethyl)phenyl]-1,3-thiazole (D67) (120 mg). δH (CDCl3, 600 MHz): 1.31 (6H, d), 4.63 (1H, m), 7.05 (1H, d), 7.70 (1H, s), 7.94 (1H, dd), 8.06 (1H, d).

Workup

customwas consumed completely
additionThe resulting solution was diluted with ethyl acetate
washThe mixture was washed with brine
dry with materialThe organic phase was dried over anhydrous sodium sulphate
customevaporated in vacuo
customThe crude product was purified by column chromatography

Sources & evidence

ORD record: ord-95c19e6858124fc9984b943c3cca13f0
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389508B2

Reaction notes

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