Boron tribromide → HCID 136388722, compound
Reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C:26]2[O:30][N:29]=[C:28]([C:31]3[C:32]([C:37]([F:40])([F:39])[F:38])=[N:33][CH:34]=[CH:35][CH:36]=3)[N:27]=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[O:30][N:29]=[C:28]([C:31]3[C:32]([C:37]([F:40])([F:39])[F:38])=[N:33][CH:34]=[CH:35][CH:36]=3)[N:27]=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
Conditions
- Temperature
- -78 °C
Procedure
A solution of 5-(3,4-bis(benzyloxy)-5-nitrophenyl)-3-(2-(trifluoromethyl)pyridin-3-yl)-1,2,4-oxadiazole (0.099 g, 0.18 mmol) in dichloromethane (5 mL) was cooled to −78° C. with stirring under argon and treated with boron tribromide (0.18 g, 0.74 mmol) dropwise. 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 the 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-(3-(2-(trifluoromethyl)pyridin-3-yl)-1,2,4-oxadiazol-5-yl)benzene-1,2-diol as a yellow solid, 0.058 g (88%).
Workup
- stirringto stir at room temperature for one hour
- customThe mixture was quenched by the 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-3c76f27d996f4517900638fee0c15618
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09446012B2
Reaction notes
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