Boron tribromide → 4H-1-Benzopyran-4-one, 3-(2,4-dihydroxyphenyl)-7-hydroxy-

HRID 1357062ノート

反応式

HRID 1357062 の反応式
C[O:2][C:3]1[CH:8]=[C:7]([O:9]C)[CH:6]=[CH:5][C:4]=1[C:11]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][C:16]([O:22]C)=[CH:17][CH:18]=2)[O:13][CH:12]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:8]=[C:7]([OH:9])[CH:6]=[CH:5][C:4]=1[C:11]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][C:16]([OH:22])=[CH:17][CH:18]=2)[O:13][CH:12]=1

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 140183653-(2,4-Dimethoxyphenyl)-7-methoxy-4H-1-benzopyran-4-one

生成物 1

HCID 52805204H-1-Benzopyran-4-one, 3-(2,4-dihydroxyphenyl)-7-hydroxy-収率 57.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

At 0° C., a solution of 14 (1.0 g, 3.2 mmol) in CH2Cl2 was treated with BBr3 (16 mL, 16 mmol, 1 M in CH2Cl2) and the reaction mixture was allowed to stir at rt for 18 h. The reaction was quenched slowly with MeOH, concentrated and taken up in EtOAc. The EtOAc layer was washed with 2N HCl aq. And the EtOAc was dried over MgSO4, filtered, concentrated and chromatographed on silica gel (EtOAC/hexanes; 1:1) to yield 15 as a white solid (0.5 g).

後処理

  1. customThe reaction was quenched slowly with MeOH
  2. concentrationconcentrated
  3. washThe EtOAc layer was washed with 2N HCl aq.
  4. dry with materialthe EtOAc was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed on silica gel (EtOAC/hexanes; 1:1)

出典と根拠

ORDレコード
ord-e58ff85d164f434ab31246de31256286
出典データセット
uspto-grants-2003_07
特許番号
US06589980B2

反応ノート

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