Sodium hydride → 1-(4-Bromo-2-nitro-phenoxy)-cyclopropanecarboxylic acid ethyl ester

HRID 1258833노트

반응식

HRID 1258833 반응식
[CH2:1]([O:3][C:4]([C:6]1([OH:9])[CH2:8][CH2:7]1)=[O:5])[CH3:2].[H-].[Na+].C1OCCOCCOCCOCCOC1.[Br:27][C:28]1[CH:33]=[CH:32][C:31](O)=[C:30]([N+:35]([O-:37])=[O:36])[C:29]=1F>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1([O:9][C:31]2[CH:32]=[CH:33][C:28]([Br:27])=[CH:29][C:30]=2[N+:35]([O-:37])=[O:36])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

참가 물질

6

반응물 4

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 2733706Ethyl 1-hydroxycyclopropane-1-carboxylateHCID 534048764-Bromo-3-fluoro-2-nitrophenol

생성물 1

HCID 583407841-(4-Bromo-2-nitro-phenoxy)-cyclopropanecarboxylic acid ethyl ester수율 51.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of ethyl-1-hydroxycyclopropane carboxylate (2.93 g, 20.5 mmol) in THF (50 mL) was added sodium hydride (60% in mineral oil, 981 mg, 24.5 mmol) under argon atmosphere. After 10 min, 15-crown-5 (0.2 mL) followed by 4-bromo-2-nitro-fluorophenol (4.5 g, 20.5 mmol) were added. The reaction mixture was stirred at room temperature overnight then quenched by the addition of methanol (1.5 mL) and diluted with ethyl acetate. The mixture was washed with brine, and the organic layer was dried over anhydrous sodium sulfate, concentrated and purified by silica gel column chromatography to give 1-(4-bromo-2-nitro-phenoxy)-cyclopropanecarboxylic acid ethyl ester (3.51 g).

후처리

  1. additionwere added
  2. customthen quenched by the addition of methanol (1.5 mL)
  3. additiondiluted with ethyl acetate
  4. washThe mixture was washed with brine
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-3e96af10336743b39d11cdf382a2ee31
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08466114B2

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