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

HRID 1294364

Reaction equation

HRID 1294364 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]CC)=[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 66578655ethyl (1R,2R)-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 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-(4-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-01d029b9507845d591f84661edc5446c
Source dataset
uspto-grants-2007_07
Patent number
US07238706B2

Linked notes

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