Boron tribromide → HCID 136388717, compound

HRID 42653Notes

Reaction equation

HRID 42653 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:14]2[C:18]([C:19]3[C:20]([C:25]([F:28])([F:27])[F:26])=[N:21][CH:22]=[CH:23][CH:24]=3)=[CH:17][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>[N+:11]([C:7]1[CH:6]=[C:5]([C:14]2[C:18]([C:19]3[C:20]([C:25]([F:28])([F:27])[F:26])=[N:21][CH:22]=[CH:23][CH:24]=3)=[CH:17][O:16][N:15]=2)[CH:4]=[C:3]([OH:2])[C:8]=1[OH:9])([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 687050003-(3,4-Dimethoxy-5-nitrophenyl)-4-(2-(trifluoromethyl)pyridin-3-yl)isoxazole

Product 1

HCID 136388717HCID 136388717, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(3,4-dimethoxy-5-nitrophenyl)-4-(2-(trifluoromethyl)pyridin-3-yl)isoxazole (0.79 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-nitro-5-(4-(2-(trifluoromethyl)pyridin-3-yl)isoxazol-3-yl)benzene-1,2-diol as a yellow solid, 0.47 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-ebaa1e3f5c6543bb87b1191c46f9de8b
Source dataset
uspto-grants-2013_09
Patent number
US08536203B2

Reaction notes

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