Boron tribromide → HCID 136350296, compound

HRID 1506450Notes

Reaction equation

HRID 1506450 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:28](=[CH:29][C:30]=1[CH3:31])[C:9]1=[N:10][O:11][C:12]([C:13]3[C:17]([C:18]([F:21])([F:20])[F:19])=[C:16]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[O:15][N:14]=3)=[C:8]1[CH2:7][CH2:6]2.B(Br)(Br)Br>ClCCl>[CH3:31][C:30]1[CH:29]=[C:28]2[C:5]([CH2:6][CH2:7][C:8]3[C:9]2=[N:10][O:11][C:12]=3[C:13]2[C:17]([C:18]([F:21])([F:20])[F:19])=[C:16]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[O:15][N:14]=2)=[CH:4][C:3]=1[OH:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 67172443HCID 67172443, compound

Product 1

HCID 136350296HCID 136350296, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 7-methoxy-8-methyl-3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazole (Preparation 64B, 0.130 g, 0.305 mmol) in dichloromethane (5 mL) at 0° C. was added boron tribromide (1.52 mL, 1.52 mmol). The reaction mixture was stirred at 0° C. for 1 h and then allowed to warm to room temperature and stirred overnight. The reaction mixture was partitioned between dichloromethane (25 mL) and water (25 mL). The dichloromethane extract was washed with a saturated aqueous solution of sodium bicarbonate (2×25 mL), washed with brine, dried over sodium sulfate, and concentrated. This crude product was filtered through a short silica gel pad, and the filtrate was concentrated to give 8-methyl-3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-ol (0.121 g, 0.293 mmol, 96%) as a tan solid. The product had an HPLC ret. time=4.08 min (condition B). LC/MS M+1=413.30.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred overnight
  3. customThe reaction mixture was partitioned between dichloromethane (25 mL) and water (25 mL)
  4. extractionThe dichloromethane extract
  5. washwas washed with a saturated aqueous solution of sodium bicarbonate (2×25 mL)
  6. washwashed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. filtrationThis crude product was filtered through a short silica gel pad
  10. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-aea54db8677c47b5a9000884f307065c
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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