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

HRID 2110746Notes

Reaction equation

HRID 2110746 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-fc2c2e2a1eb5435bb32f8857e3414522
Source dataset
uspto-grants-2009_04
Patent number
US07517889B2

Reaction notes

Loading…