Cesium carbonate → Methyl 3-(3-(((4-bromo-3-methylphenyl)methyl)oxy)phenyl)propanoate

HRID 1662310노트

반응식

HRID 1662310 반응식
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Br:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27]Cl)=[CH:23][C:22]=1[CH3:29]>CN(C=O)C.O>[Br:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][O:1][C:2]2[CH:3]=[C:4]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:5]=[CH:6][CH:7]=2)=[CH:23][C:22]=1[CH3:29]

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 1512675Methyl 3-(3-hydroxyphenyl)propionateHCID 189606101-Bromo-4-(chloromethyl)-2-methylbenzene

생성물 1

HCID 57705740Methyl 3-(3-(((4-bromo-3-methylphenyl)methyl)oxy)phenyl)propanoate수율 90.8%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To flask containing methyl 3-(3-hydroxyphenyl)propanoate (available from Aagile Labs Division of Tyger Scientific) (0.25 g, 1.387 mmol) and cesium carbonate (0.5876 g, 1.804 mmol) in DMF (8 mL), was added 1.2 (0.3654 g, 1.665 mmol). The resulting mixture was then stirred overnight. The reaction was diluted with water and extracted with EtOAc. The organic layers were washed with brine, dried over Na2SO4, filtered, concentrated, and then purified by combiflash (0 to 20% EtOAc/hexane) to provide 1.3 (0.4575 g, 90.78% yield). MS ESI (pos.) m/e: 382.0 (M+H2O)+.

후처리

  1. extractionextracted with EtOAc
  2. washThe organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by combiflash (0 to 20% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-ddb01c2074b141bda272d99f1161faa4
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030354B2

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