Lithium Hydroxide → 2-(4-Bromophenyl)cyclopropanecarboxylic acid

HRID 1392701Notes

Reaction equation

HRID 1392701 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:10][C@H:9]2[C:11]([O:13]C)=[O:12])=[CH:4][CH:3]=1.[Li+].[OH-]>C1COCC1.CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:10][CH:9]2[C:11]([OH:13])=[O:12])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 69159174cis-Methyl 2-(4-bromophenyl)cyclopropanecarboxylate

Product 1

HCID 3015412-(4-Bromophenyl)cyclopropanecarboxylic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ester from step 2 in THF-MeOH (4:1, 0.5M) was added LiOH (3 eq, 2M) and the mixture was stirred at 50° C. for 1 h. The organic solvent was evaporated, the aqueous layer was acidified with HCl 1N and the acid extracted with EtOAc (3×). The combined organic extracts were washed with brine, dried and evaporated to afford 2-(4-bromophenyl)cyclopropanecarboxylic acid. Optically active intermediates were obtained by separation on chiral column (Chiral Pak AD) using hexane:EtOH (90:10 with 0.2% TFA)

Workup

  1. customThe organic solvent was evaporated
  2. extractionthe acid extracted with EtOAc (3×)
  3. washThe combined organic extracts were washed with brine
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-7d41fceb5be1484ea087a56183bb0df3
Source dataset
uspto-grants-2008_03
Patent number
US07342024B2

Reaction notes

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