Propiolic Acid → 4-Bromo-3,5-dimethylphenyl propiolate

HRID 1483185노트

반응식

HRID 1483185 반응식
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].[C:11](O)(=[O:14])[C:12]#[CH:13].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:11]([O:9][C:5]1[CH:6]=[C:7]([CH3:8])[C:2]([Br:1])=[C:3]([CH3:10])[CH:4]=1)(=[O:14])[C:12]#[CH:13]

참가 물질

6

반응물 3

HCID 10110Propiolic AcidHCID 10868DicyclohexylcarbodiimideHCID 819704-Bromo-3,5-dimethylphenol

생성물 1

HCID 725452334-Bromo-3,5-dimethylphenyl propiolate수율 51%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

To a stirred solution of 4-bromo-3,5-dimethylphenol (40.87 g, 203.3 mmol) and propiolic acid (20.91 g, 298.5 mmol) in CH2Cl2 (400 mL) was added DCC (50.78 g, 246.1 mmol) in CH2Cl2 (100 mL) and DMAP (0.82 g, 6.7 mmol) at 0° C. The mixture was stirred at room temperature for 3 h and filtered. The filtrate was concentrated and purified by silica gel column chromatography (hexanes:EtOAc:CH2Cl2=20:1:10). The fractions containing the desired compound were concentrated. To the concentrate added hexane and the precipitated solid was collected by filtration. The solid was washed with hexane and dried to give the title compound 6-1 (26.12 g, 51% yield) as a white solid.

후처리

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. custompurified by silica gel column chromatography (hexanes:EtOAc:CH2Cl2=20:1:10)
  4. additionThe fractions containing the desired compound
  5. concentrationwere concentrated
  6. additionTo the concentrate added hexane
  7. filtrationthe precipitated solid was collected by filtration
  8. washThe solid was washed with hexane
  9. customdried

출처 및 근거

ORD 기록
ord-53954c35f7804a46a5de309dfd918267
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09416121B2

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