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

HRID 490764노트

반응식

HRID 490764 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4d83453efe114214a324cc8e36c1b42f
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528160B2

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