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

HRID 873720노트

반응식

HRID 873720 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
135 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-98fb229585bf4e17a00a4c0259845591
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08975415B2

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