Boron tribromide → 3-(6-Fluoro-benzo[d]isoxazol-3-yl)-phenol

HRID 852080Notes

Reaction equation

HRID 852080 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:5]2[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([O:15]C)[CH:10]=3)=[N:7][O:8][C:4]=2[CH:3]=1.B(Br)(Br)Br>ClCCl>[F:1][C:2]1[CH:18]=[CH:17][C:5]2[C:6]([C:9]3[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=3)=[N:7][O:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 179062626-Fluoro-3-(3-methoxy-phenyl)-benzo[d]isoxazole

Product 1

HCID 179062783-(6-Fluoro-benzo[d]isoxazol-3-yl)-phenolYield 95.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Combine 6-fluoro-3-(3-methoxy-phenyl)-benzo[d]isoxazole (30 g, 0.123 mol) and dichloromethane (anhydrous, 360 mL) under nitrogen atmosphere and cool (0° C.). Slowly add 1.0 M solution of boron tribromide in dichloromethane (370 mL, 0.370 mol) over 1 hour and stir at 0° C. for 3 hours. TLC indicates that all starting material is consumed. Quench the reaction mixture with 150 mL methanol, concentrate and azeotrope off the boron tribromide two more times with methanol. Dissolve the material in ethyl acetate, wash with K2CO3, saturated sodium chloride, dry (MgSO4) and concentrate. Triturate in heptane:dichloromethane (9:1), filter and wash with heptane and dry in the oven to give the title compound (26.93 g, 95% Yield). NMR and microanalysis (C, H, N) are consistent with the final, desired compound. mp=144-145° C.

Workup

  1. customis consumed
  2. customQuench the reaction mixture with 150 mL methanol
  3. concentrationconcentrate
  4. dissolutionDissolve the material in ethyl acetate
  5. washwash with K2CO3, saturated sodium chloride
  6. dry with materialdry (MgSO4)
  7. concentrationconcentrate
  8. customTriturate in heptane:dichloromethane (9:1)
  9. filtrationfilter
  10. washwash with heptane
  11. customdry in the oven

Sources & evidence

ORD record
ord-0134904e1d2f49d2a542ae89e731dab2
Source dataset
uspto-grants-2007_08
Patent number
US07253165B2

Reaction notes

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