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Potassium Iodide → 4-(3-Bromo-propoxy)-3-fluorobenzoic acid ethyl ester

HRID 220868
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HRID 220868 반응식
[Br:1][CH2:2][CH2:3][CH2:4]Br.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH2:14]([O:16][C:17](=[O:26])[C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([F:25])[CH:19]=1)[CH3:15]>CC(C)=O>[CH2:14]([O:16][C:17](=[O:26])[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:4][CH2:3][CH2:2][Br:1])=[C:20]([F:25])[CH:19]=1)[CH3:15]
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참가 물질

6

반응물 4

HCID 4875Potassium IodideHCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 13745619Ethyl 3-fluoro-4-hydroxybenzoate

생성물 1

HCID 575553074-(3-Bromo-propoxy)-3-fluorobenzoic acid ethyl ester수율 71%

시약·촉매·용매 1

HCID 180Acetone
용매

실험 절차

1,3-Dibromopropane (2.2 g, 11.0 mmol), potassium carbon-ate (1.86 g, 13.6 mmol) and potassium iodide (90 mg, 0.5 mmol) were added to 3-fluoro-4-hydroxy-benzoic acid ethyl ester from Example E27 (11.0 g, 5.4 mmol) in acetone (25 ml) and the mixture was heated at reflux for 20 h. The solid was filtered off and washed with EtOAc. The filtrate was concentrated in vacuo and azeotroped with toluene. The residue was purified by flash chromatography on silica gel (eluant; 20% EtOAc:80% hexane) to yield the title compound (1.18 g, 71%).

후처리

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 20 h
  3. filtrationThe solid was filtered off
  4. washwashed with EtOAc
  5. concentrationThe filtrate was concentrated in vacuo
  6. customazeotroped with toluene
  7. customThe residue was purified by flash chromatography on silica gel (eluant; 20% EtOAc:80% hexane)

출처 및 근거

ORD 기록
ord-a829fcad336b485abe87ea058af5c1cb
출처 데이터셋
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08202858B2

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