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

HRID 2209277

반응식

HRID 2209277 반응식
[H-].[Na+].[OH:3][C:4]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:6][CH2:5]1.[Br:12][C:13]1[CH:18]=[CH:17][C:16](F)=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=1>C1COCC1.C1OCCOCCOCCOCCOC1.C(OCC)(=O)C>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([O:3][C:4]2([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:6][CH2:5]2)=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=1

참가 물질

7

반응물 3

HCID 24758Sodium hydrideHCID 2733706Ethyl 1-hydroxycyclopropane-1-carboxylateHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

생성물 1

HCID 583407841-(4-Bromo-2-nitro-phenoxy)-cyclopropanecarboxylic acid ethyl ester수율 66.6%

시약·촉매·용매 3

HCID 3633615-Crown-5촉매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

Sodium hydride (60%, 166 mg, 4.15 mmol) was added to a solution of ethyl 1-hydroxycyclopropanecarboxylate (0.41 mL, 3.59 mmol) in THF (10 mL) at room temperature. After 15 min, 3 drops of 15-crown-5 were added followed by 4-bromo-1-fluoro-2-nitrobenzene (0.42 mL, 3.41 mmol). Mixture was stirred at room temperature for 24 hours. After diluting with 50 mL of ethyl acetate, mixture was quenched by addition of brine (25 mL) and layers were separated. Aqueous phase was extracted with ethyl acetate and combined organics were dried (MgSO4), filtered, and concentrated under reduced pressure. Resulting residue was purified via silica gel column chromatography (0-30% ethyl acetate/hexanes) to yield ethyl 1-(4-bromo-2-nitrophenoxy)cyclopropanecarboxylate 7.20 (750 mg)

후처리

  1. customwas quenched by addition of brine (25 mL) and layers
  2. customwere separated
  3. extractionAqueous phase was extracted with ethyl acetate
  4. dry with materialcombined organics were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customResulting residue was purified via silica gel column chromatography (0-30% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-faca75f7960544ebb89e4f0a3c66e48f
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09376441B2

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