Potassium Carbonate → 4-(4-Acetyl-3-chlorophenoxy)benzonitrile

HRID 1095899

반응식

HRID 1095899 반응식
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].[CH3:10][C:11]([C:13]1[CH:18]=[CH:17][C:16](F)=[CH:15][C:14]=1[Cl:20])=[O:12].C([O-])([O-])=O.[K+].[K+].CCCCCCC.CCOC(C)=O>CC(N(C)C)=O.O>[C:11]([C:13]1[CH:18]=[CH:17][C:16]([O:9][C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)=[CH:15][C:14]=1[Cl:20])(=[O:12])[CH3:10]

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 130194-CyanophenolHCID 27365072'-Chloro-4'-fluoroacetophenoneHCID 21899848Ethylacetate heptane

생성물 1

HCID 643355014-(4-Acetyl-3-chlorophenoxy)benzonitrile

시약·촉매·용매 2

HCID 962Water용매HCID 31374Dimethylacetamide용매

실험 절차

To a solution 4-cyanophenol (CAS Reg. No. 767-00-0, 1.2 g), 2-chloro-4-fluoroacetophenone (CAS Reg. No. 700-35-6, 1.7 g) in DMA (10 ml) was added K2CO3 (1.66 g). The mixture is refluxed for 5 h. TLC (heptane/EtOAc 2:1) showed complete conversion. Water was added and the mixture was extracted with DCM. The combined organic layers were dried over Na2SO4 and then concentrated to an oil. The residue was purified by flash chromatography (SiO2, EtOAc/heptane 1:2) to give the title compound (1.8 g) as yellow oil. MS (m/e)=272.2 [M+H+].

후처리

  1. temperatureThe mixture is refluxed for 5 h
  2. extractionthe mixture was extracted with DCM
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated to an oil
  5. customThe residue was purified by flash chromatography (SiO2, EtOAc/heptane 1:2)

출처 및 근거

ORD 기록
ord-dc8398acd11a40ffbe7b23aa940ad840
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08138189B2

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