Boron tribromide → 3-Nitro-5-(2-(2-(trifluoromethyl)pyridin-3-yl)thiazol-4-yl)benzene-1,2-diol
Reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C:26]2[N:27]=[C:28]([C:31]3[C:32]([C:37]([F:40])([F:39])[F:38])=[N:33][CH:34]=[CH:35][CH:36]=3)[S:29][CH:30]=2)[CH:12]=[C:13]([N+:23]([O-:25])=[O:24])[C:14]=1[O:15]CC1C=CC=CC=1)C1C=CC=CC=1.B(Br)(Br)Br>ClCCl>[N+:23]([C:13]1[CH:12]=[C:11]([C:26]2[N:27]=[C:28]([C:31]3[C:32]([C:37]([F:40])([F:39])[F:38])=[N:33][CH:34]=[CH:35][CH:36]=3)[S:29][CH:30]=2)[CH:10]=[C:9]([OH:8])[C:14]=1[OH:15])([O-:25])=[O:24]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 4-(3,4-bis(benzyloxy)-5-nitrophenyl)-2-(2-(trifluoromethyl)pyridin-3-yl)thiazole (0.146 g, 0.26 mmol), in dichloromethane (10 mL) was cooled to −78° C. and treated under argon, with boron tribromide (0.26 g, 1.03 mmol). The resulting deep purple suspension was then allowed to stir at room temperature for one hour before cooling again to −78° C. The mixture was quenched by careful addition of methanol. After stirring at room temperature for thirty minutes, the volatiles were evaporated and the residue stirred with 2 N hydrochloric acid (5 mL) for thirty minutes. The resulting solid was filtered off, washed with water (25 mL) and then cold isopropanol (5 mL) to give 3-nitro-5-(2-(2-(trifluoromethyl)pyridin-3-yl)thiazol-4-yl)benzene-1,2-diol as a yellow solid, 0.087 g (87%).
Workup
- temperaturebefore cooling again to −78° C
- customThe mixture was quenched by careful addition of methanol
- stirringAfter stirring at room temperature for thirty minutes
- customthe volatiles were evaporated
- stirringthe residue stirred with 2 N hydrochloric acid (5 mL) for thirty minutes
- filtrationThe resulting solid was filtered off
- washwashed with water (25 mL)
Sources & evidence
- ORD record
- ord-9ef7960cb22949c4949d590a13766a3f
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09446012B2
Reaction notes
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