Boron tribromide → HCID 67036905, compound

HRID 1401296Notes

Reaction equation

C[O:2][C:3]1[CH:4]=[C:5]([C:14]2[C:15]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:16]([C:19]3[C:20]([C:26]([F:29])([F:28])[F:27])=[N+:21]([O-:25])[CH:22]=[CH:23][CH:24]=3)[O:17][CH:18]=2)[CH:6]=[C:7]([N+:11]([O-:13])=[O:12])[C:8]=1[O:9]C.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]([C:14]2[C:15]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:16]([C:19]3[C:20]([C:26]([F:28])([F:29])[F:27])=[N+:21]([O-:25])[CH:22]=[CH:23][CH:24]=3)[O:17][CH:18]=2)[CH:6]=[C:7]([N+:11]([O-:13])=[O:12])[C:8]=1[OH:9]

Participants

Conditions

Temperature: -78 °C

Procedure

3-(4-(3,4-Dimethoxy-5-nitrophenyl)-3-(ethoxycarbonyl)furan-2-yl)-2-(trifluoro-methyl)pyridine-1-oxide (482 mg, 1 mmol) was taken up in dichloromethane (8 mL). The yellowish suspension was cooled to −78° C. under argon and boron tribromide (0.85 mL, 9 mmol) was added dropwise. The reddish reaction mixture was allowed to warm to room temperature and stirred for 18 hours and then carefully poured into ice-water (100 mL) and stirred for 1 hour. The yellow precipitate was filtered off, washed with water and dried over P2O5 under vacuum. Recrystallisation of the solid from ethanol gave 3-(4-(3,4-Dihydroxy-5-nitrophenyl)-3-(ethoxycarbonyl)furan-2-yl)-2-(trifluoromethyl)pyridine 1-oxide as a yellow solid, 0.31 g (68%).

Workup

customThe reddish reaction mixture
temperatureto warm to room temperature
stirringstirred for 1 hour
filtrationThe yellow precipitate was filtered off
washwashed with water
dry with materialdried over P2O5 under vacuum
customRecrystallisation of the solid from ethanol

Sources & evidence

ORD record: ord-e9570b44a6f246618d93495195a72547
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08907099B2

Reaction notes

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