1,4-Dibromobutane → Ethyl 1-(3-bromophenyl)cyclopentanecarboxylate

HRID 216217Notes

Reaction equation

HRID 216217 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Br:14])[CH:9]=1)[CH3:4].C1OCCOCCOCCOCCOCCOC1.Br[CH2:35][CH2:36][CH2:37][CH2:38]Br>CN(C=O)C.O>[CH2:3]([O:5][C:6]([C:7]1([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Br:14])[CH:9]=2)[CH2:38][CH2:37][CH2:36][CH2:35]1)=[O:15])[CH3:4]

Participants

7

Reactant 4

HCID 80561,4-DibromobutaneHCID 24758Sodium hydrideHCID 2855718-Crown-6HCID 11470552Ethyl 3-(bromophenyl)acetate

Product 1

HCID 69071358Ethyl 1-(3-bromophenyl)cyclopentanecarboxylateYield 91.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% in oil, 1.07 g, 26.8 mmol) is added to a solution of (3-bromo-phenyl)-acetic acid ethyl ester [2.59 g, 10.7 mmol] and 18-crown-6 (catalytic amount) in N,N′-dimethylformamide (50 mL). The mixture is stirred for 25 minutes and 1,4-dibromobutane (1.41 mL, 11.8 mmol) is added dropwise via syringe. The mixture is stirred for 18 hours at ambient temperature, diluted with water (100 mL) and extracted thrice with EtOAc (60 mL). The organic extracts are combined and dried over magnesium sulfate, filtered and concentrated to afford 1-(3-bromo-phenyl)-cyclopentanecarboxylic acid ethyl ester [2.9 g, 91%] as an oil, which is used without further purification.

Workup

  1. stirringThe mixture is stirred for 18 hours at ambient temperature
  2. extractionextracted thrice with EtOAc (60 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a00b33af7e924d9bbc59240a8dc8f0f3
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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