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

HRID 334046

反応式

HRID 334046 の反応式
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]

参加物

6

反応物 2

HCID 90488Ethyl 3-bromobenzoateHCID 178419768HCID 178419768、化合物

生成物 1

HCID 866882776-Cyclopentyl-benzoic acid ethyl ester

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
85 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-592a1af4737c4ee3975dbeaebcb1cea7
出典データセット
uspto-grants-2014_11
特許番号
US08883789B2

関連ノート

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