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

HRID 220868
ノート
印刷プレビュー

反応式

HRID 220868 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone
溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-a829fcad336b485abe87ea058af5c1cb
出典データセット
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08202858B2

反応ノート

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