Boron tribromide → Ethyl 6-hydroxybenzofuran-3-carboxylate

HRID 250273노트

반응식

HRID 250273 반응식
[CH2:1]([O:3][C:4]([C:6]1[C:10]2[CH:11]=[CH:12][C:13]([O:15]C)=[CH:14][C:9]=2[O:8][CH:7]=1)=[O:5])[CH3:2].B(Br)(Br)Br>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[C:10]2[CH:11]=[CH:12][C:13]([OH:15])=[CH:14][C:9]=2[O:8][CH:7]=1)=[O:5])[CH3:2]

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 45489697Ethyl 6-methoxybenzofuran-3-carboxylate

생성물 1

HCID 59152646Ethyl 6-hydroxybenzofuran-3-carboxylate수율 68%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

A −78° C. solution of 6-methoxy-benzofuran-3-carboxylic acid ethyl ester (1.50 g, 6.81 mmol) in dichloromethane (20 mL) is treated with boron tribromide (20 mL) dropwise. The mixture is stirred at 0° C. for 60 minutes. The reaction is quenched by adding MeOH (10 mL) dropwise over 10 minutes. The mixture is concentrated. The residue is purified via flash chromatography eluting with 25% EtOAc/hexanes to provide the title compound (0.95 g, 68%). ES/MS m/e 207.0 (M+1), 205.0 (M−1).

후처리

  1. customThe reaction is quenched
  2. additionby adding MeOH (10 mL) dropwise over 10 minutes
  3. concentrationThe mixture is concentrated
  4. customThe residue is purified via flash chromatography
  5. washeluting with 25% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-8b21c22bbc2d46c2bf3a1ead6bbc9c07
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863302B2

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