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

HRID 852080ノート

反応式

HRID 852080 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0134904e1d2f49d2a542ae89e731dab2
出典データセット
uspto-grants-2007_08
特許番号
US07253165B2

反応ノート

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