Methanol → 1-(3-Bromophenyl)cyclopentane-1-carboxylic acid

HRID 216218Notes

Reaction equation

HRID 216218 reaction equation
C([O:3][C:4]([C:6]1([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Br:17])[CH:12]=2)[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5])C.[OH-].[Li+].C1COCC1.CO>O>[Br:17][C:13]1[CH:12]=[C:11]([C:6]2([C:4]([OH:5])=[O:3])[CH2:10][CH2:9][CH2:8][CH2:7]2)[CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 69071358Ethyl 1-(3-bromophenyl)cyclopentanecarboxylate

Product 1

HCID 157427251-(3-Bromophenyl)cyclopentane-1-carboxylic acidYield 80.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-(3-bromo-phenyl)-cyclopentanecarboxylic acid ethyl ester [3.42 g, 11.51 mmol], lithium hydroxide (579 mg, 13.81 mmol), THF (13 mL), MeOH (13 mL) and water (13 mL) is vigorously stirred for 18 hours. The mixture is concentrated and the residue is diluted with water (50 mL). The aqueous mixture is acidified with concentrated HCl to pH 1 and extracted twice with EtOAc (50 mL). The organic extracts are combined and dried over magnesium sulfate, filtered and concentrated to afford 1-(3-bromo-phenyl)-cyclopentanecarboxylic acid [2.5 g, 80.6%] as a solid, which is used without further purification.

Workup

  1. concentrationThe mixture is concentrated
  2. additionthe residue is diluted with water (50 mL)
  3. extractionextracted twice with EtOAc (50 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e7b07695a5854411882b8793632115d6
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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