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

HRID 230885노트

반응식

HRID 230885 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-924567b9069b486491da325b22f6a0e5
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07566699B2

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