4-Bromophenol → Ethyl 1-((4-bromophenoxy)methyl)cyclobutanecarboxylate

HRID 873720ノート

反応式

HRID 873720 の反応式
CS([O:5][CH2:6][C:7]1([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:10][CH2:9][CH2:8]1)(=O)=O.[Br:16][C:17]1[CH:22]=[CH:21][C:20](O)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Br:16][C:17]1[CH:22]=[CH:21][C:20]([O:5][CH2:6][C:7]2([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:10][CH2:9][CH2:8]2)=[CH:19][CH:18]=1

参加物

5

反応物 3

HCID 78084-BromophenolHCID 10796Cesium carbonateHCID 86724246Ethyl 1-{[(methylsulfonyl)oxy]methyl}cyclobutanecarboxylate

生成物 1

HCID 86724262Ethyl 1-((4-bromophenoxy)methyl)cyclobutanecarboxylate収率 46.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
135 °C

実験手順

The mixture of ethyl 1-{[(methylsulfonyl)oxy]methyl}cyclobutanecarboxylate (1.50 g, 6.3 mmol), 4-bromophenol (1.2 g, 7.0 mmol), and caesium carbonate (4.13 g, 7.0 mmol) in DMF (15 ml) was stirred for 6 hours at 135° C. After dilution with EtOAc and H2O, the organic layer was washed with H2O, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel chromatography (hexane:EtOAc=100:0-70:30) to give ethyl 1-[(4-bromophenoxy)methyl]cyclobutanecarboxylate (919 mg).

後処理

  1. washAfter dilution with EtOAc and H2O, the organic layer was washed with H2O
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel chromatography (hexane:EtOAc=100:0-70:30)

出典と根拠

ORDレコード
ord-98fb229585bf4e17a00a4c0259845591
出典データセット
uspto-grants-2015_03
特許番号
US08975415B2

反応ノート

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