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

HRID 852080노트

반응식

HRID 852080 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0134904e1d2f49d2a542ae89e731dab2
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253165B2

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