Potassium Iodide → 4-(4-Bromo-butoxy)-3-fluoro-benzoic Acid Ethyl Ester

HRID 220910ノート

反応式

HRID 220910 の反応式
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5]Br.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH2:15]([O:17][C:18](=[O:27])[C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([F:26])[CH:20]=1)[CH3:16]>CC(C)=O>[CH2:15]([O:17][C:18](=[O:27])[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:5][CH2:4][CH2:3][CH2:2][Br:1])=[C:21]([F:26])[CH:20]=1)[CH3:16]

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 13745619Ethyl 3-fluoro-4-hydroxybenzoate

生成物 1

HCID 575552954-(4-Bromo-butoxy)-3-fluoro-benzoic Acid Ethyl Ester収率 80%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

1,4-Dibromobutane (2.34 g, 10.8 mmol), potassium carbon-ate (1.86 g, 13.5 mmol) and potassium iodide (90 mg, 0.5 mmol) were added to a solution of 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, washed with EtOAc and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 15% EtOAc:85% hexane) to yield the title compound (1.38 g, 80%).

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. customThe residue was purified by flash chromatography on silica gel (eluant; 15% EtOAc:85% hexane)

出典と根拠

ORDレコード
ord-090972bc6b084d419a5bc596c5737e56
出典データセット
uspto-grants-2012_06
特許番号
US08202858B2

反応ノート

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