Boron tribromide → HCID 136378002, compound

HRID 1920070Notes

Reaction equation

HRID 1920070 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:14]2[CH:18]=[C:17]([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:16][N:15]=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[CH:18]=[C:17]([C:19]3[C:20]([C:26]([F:27])([F:29])[F:28])=[N+:21]([O-:25])[CH:22]=[CH:23][CH:24]=3)[O:16][N:15]=2)[CH:6]=[C:7]([N+:11]([O-:13])=[O:12])[C:8]=1[OH:9]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 67037142HCID 67037142, compound

Product 1

HCID 136378002HCID 136378002, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(3-(3,4-dimethoxy-5-nitrophenyl)isoxazol-5-yl)-2-(trifluoromethyl)pyridine 1-oxide (0.81 g, 2 mmol) was taken up in dichloromethane (15 mL) and the yellowish suspension was cooled to −78° C. under argon whereupon boron tribromide (4.5 g, 18 mmol) was added dropwise. The reddish reaction mixture was allowed to warm to room temperature and stirred for 18 hours, then carefully poured into ice-water (100 mL) and allowed to stir for 1 hour. The yellow precipitate was filtered off, washed with water and dried over P2O5 under vacuum. Trituration with boiling ethanol gave 3-(3-(3,4-dihydroxy-5-nitrophenyl)isoxazol-5-yl)-2-(trifluoromethyl)pyridine 1-oxide as a yellow solid, 0.49 g (64%).

Workup

  1. additionwas added dropwise
  2. customThe reddish reaction mixture
  3. stirringto stir for 1 hour
  4. filtrationThe yellow precipitate was filtered off
  5. washwashed with water
  6. dry with materialdried over P2O5 under vacuum

Sources & evidence

ORD record
ord-ce926148824f4bda9dd02e15823cd9aa
Source dataset
uspto-grants-2012_05
Patent number
US08168793B2

Reaction notes

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