Boron tribromide → Ethyl 6-hydroxybenzofuran-3-carboxylate

HRID 250273ノート

反応式

HRID 250273 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 59152646Ethyl 6-hydroxybenzofuran-3-carboxylate収率 68%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8b21c22bbc2d46c2bf3a1ead6bbc9c07
出典データセット
uspto-grants-2011_01
特許番号
US07863302B2

反応ノート

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