Boron tribromide → 4-Hydroxy-3-(2-phenylethyl)benzo[b]thiophene

HRID 230885ノート

反応式

HRID 230885 の反応式
C[O:2][C:3]1[C:11]2[C:10]([CH2:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:9][S:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.B(Br)(Br)Br.C(=O)([O-])O.[Na+]>ClCCl>[OH:2][C:3]1[C:11]2[C:10]([CH2:12][CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:9][S:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

参加物

5

反応物 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 231035114-Methoxy-3-(2-phenylethyl)benzo[b]thiophene

生成物 1

HCID 231035674-Hydroxy-3-(2-phenylethyl)benzo[b]thiophene収率 90.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 4-methoxy-3-(2-phenylethyl)benzo-[b]thiophene (0.77 g) in dichloromethane (25 mL) was added boron tribromide (0.54 mL) at −78° C., and the mixture was stirred at room temperature overnight. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution, and the resulting mixture was extracted with diethylether. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=6/1) to give the title compound (0.66 g).

後処理

  1. extractionthe resulting mixture was extracted with diethylether
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=6/1)

出典と根拠

ORDレコード
ord-924567b9069b486491da325b22f6a0e5
出典データセット
uspto-grants-2009_07
特許番号
US07566699B2

反応ノート

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