Boron tribromide → 2-(4-Hydroxy-phenyl)-benzo[b]thiophene-6-carboxylic Acid Methyl Ester

HRID 424791노트

반응식

HRID 424791 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=3)[S:10][C:9]=2[CH:21]=1)=[O:4].B(Br)(Br)Br>ClCCl>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)[S:10][C:9]=2[CH:21]=1)=[O:4]

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 574432832-(4-Methoxy-phenyl)-benzo[b]thiophene-6-carboxylic acid methyl ester

생성물 1

HCID 179625242-(4-Hydroxy-phenyl)-benzo[b]thiophene-6-carboxylic Acid Methyl Ester수율 12%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 2-(4-methoxy-phenyl)-benzo[b]thiophene-6-carboxylic acid methyl ester (500 mg, 1.7 mmol) in dichloromethane (15 mL) at 0° C. is added BBr3 (4.2 mL, 1 M in dichloromethane). The reaction mixture is stirred at ambient temperature overnight. The reaction is quenched by the addition of methanol and concentrated under reduced pressure. The residue is partitioned between EtOAc and 1 N HCl. The organic layer is concentrated and the residue is purified via chromatography eluting with 0 to 25% EtOAc in hexanes to give the title compound (57 mg, 12%) as a tan solid. LC-ES/MS m/e 283 (M−1).

후처리

  1. customThe reaction is quenched by the addition of methanol
  2. concentrationconcentrated under reduced pressure
  3. customThe residue is partitioned between EtOAc and 1 N HCl
  4. concentrationThe organic layer is concentrated
  5. customthe residue is purified via chromatography
  6. washeluting with 0 to 25% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-9000870e3ec24c328b74d2c11ff2df36
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106077B2

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