Lithium Hydroxide → 2-(3-Bromophenyl)cyclopropane-1-carboxylic acid

HRID 1294367Notes

Reaction equation

HRID 1294367 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[CH2:10][C@H:9]2[C:11]([O:13]C)=[O:12])[CH:5]=[CH:6][CH:7]=1.[Li+].[OH-]>C1COCC1.CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:10][CH:9]2[C:11]([OH:13])=[O:12])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 69158730HCID 69158730, compound

Product 1

HCID 226152002-(3-Bromophenyl)cyclopropane-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ester from step 1 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 evaporated, aqueous was acidified with HCl 1N and the acid extracted with EtOAc (3×). The organic was washed with brine, dried and solvent evaporated to afford 2-(3-bromophenyl)cyclopropanecarboxylic acid.

Workup

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

Sources & evidence

ORD record
ord-cc20ea3a28dc4607a48d048adce957e9
Source dataset
uspto-grants-2007_07
Patent number
US07238706B2

Reaction notes

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