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

HRID 334046

Reaction equation

HRID 334046 reaction equation
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]

Participants

6

Reactant 2

HCID 90488Ethyl 3-bromobenzoateHCID 178419768HCID 178419768, compound

Product 1

HCID 866882776-Cyclopentyl-benzoic acid ethyl ester

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
85 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-592a1af4737c4ee3975dbeaebcb1cea7
Source dataset
uspto-grants-2014_11
Patent number
US08883789B2

Linked notes

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