Ethyl 3-bromobenzoate → 6-Cyclopentyl-benzoic acid ethyl ester

HRID 334046

반응식

HRID 334046 반응식
Br[C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[Br-].[CH:14]1([Zn+])[CH2:18][CH2:17][CH2:16][CH2:15]1>C1COCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:8]([O:7][C:5](=[O:6])[C:4]1[C:10]([CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:11][CH:12]=[CH:2][CH:3]=1)[CH3:9]

참가 물질

6

반응물 2

HCID 90488Ethyl 3-bromobenzoateHCID 178419768HCID 178419768, 화합물

생성물 1

HCID 866882776-Cyclopentyl-benzoic acid ethyl ester

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
85 °C

실험 절차

To 1.00 mL (6.24 mmol) ethyl 3-bromobenzoate was added 13.0 mL (6.50 mmol) 0.5 M cyclopentylzinc bromide solution in THF followed by 100 mg (0.137 mmol) 1,1′-bis(diphenylphosphino)ferrocenedichloropalladium(II) under argon atmosphere. The reaction mixture was stirred at 85° C. for 1.5 h, then diluted with water and stirred at RT for 12 h. The suspension was extracted with EtOAc. The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was filtered through Alox (EtOAC) and concentrated in vacuo.

후처리

  1. stirringstirred at RT for 12 h
  2. extractionThe suspension was extracted with EtOAc
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. filtrationThe crude material was filtered through Alox (EtOAC)
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-592a1af4737c4ee3975dbeaebcb1cea7
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883789B2

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