Boron tribromide → (4-Hydroxy-benzo[b]thiophen-3-yl)-acetic acid ethyl ester

HRID 490764ノート

反応式

HRID 490764 の反応式
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][C:6]1[C:7]2[C:14]([O:15]C)=[CH:13][CH:12]=[CH:11][C:8]=2[S:9][CH:10]=1)[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][C:6]1[C:7]2[C:14]([OH:15])=[CH:13][CH:12]=[CH:11][C:8]=2[S:9][CH:10]=1)[CH3:2]

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 218162724-Methoxy-benzo[b]thiophen-3-yl-acetic acid ethyl ester

生成物 1

HCID 57431999(4-Hydroxy-benzo[b]thiophen-3-yl)-acetic acid ethyl ester収率 60.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of (4-Methoxy-benzo[b]thiophen-3-yl)-acetic acid ethyl ester (0.7 g, 2.8 mmol) in methylene chloride (18 mL) is added BBr3 (1.0 M, heptane, 8.6 mL, 8.6 mmol) at −20˜−30° C. The reaction mixture is allowed to warm to room temperature over 2 hrs, and TLC indicated clean conversion. The reaction is quenched by ice water, extracted with methylene chloride, dried over sodium sulfate, concentrated. Column chromatography on silica gel eluted with hexanes/ethyl acetate yields the title compound (0.4 g).

後処理

  1. customThe reaction is quenched by ice water
  2. extractionextracted with methylene chloride
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. washColumn chromatography on silica gel eluted with hexanes/ethyl acetate

出典と根拠

ORDレコード
ord-4d83453efe114214a324cc8e36c1b42f
出典データセット
uspto-grants-2009_05
特許番号
US07528160B2

反応ノート

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