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Acetic Acid → Methyl 1-(4-bromophenyl)cyclopropane-1-carboxylate

HRID 861025
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HRID 861025 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]#N)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[OH-:13].[Na+].C[C:16](O)=[O:17]>CCO.[Cl-].[Na+].O>[CH3:16][O:17][C:11]([C:8]1([C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)[CH2:10][CH2:9]1)=[O:13]
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참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 27952731-(4-Bromophenyl)Cyclopropanecarbonitrile

생성물 1

HCID 46739795Methyl 1-(4-bromophenyl)cyclopropane-1-carboxylate

시약·촉매·용매 2

HCID 702Ethanol용매HCID 57417360Sodium chloride; water용매
이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

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온도
100 °C

실험 절차

To a solution of -(4-bromo-phenyl)-cyclopropanecarbonitrile from Step 1 in EtOH (0.2M) was added NaOH 25% (10 eq.). The mixture was stirred for 6 h at 100° C., quenched with AcOH (20 eq.), poured in brine, extracted with EtOAc (2×). The combined organic extracts were dried over MgSO4, filtered and concentrated. The residue was dissolved in CH2Cl2 and diazomethane was added portionwise until the esterification was completed by TLC. Flash chromatography (Hex:EtOAc; 9:1) afforded the title compound as a colorless oil.

후처리

  1. extractionextracted with EtOAc (2×)
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in CH2Cl2
  6. additiondiazomethane was added portionwise until the esterification

출처 및 근거

ORD 기록
ord-b49024aea32b4a2eb2534955fd7ceac2
출처 데이터셋
uspto-grants-2006_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07153968B2

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