Lithium Hydroxide → 2-(3-Bromophenyl)-2-methylpropanoic acid

HRID 1392698Notes

Reaction equation

HRID 1392698 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([CH3:14])([CH3:13])[C:9]([O:11]C)=[O:10])[CH:5]=[CH:6][CH:7]=1.[Li+].[OH-]>C1COCC1.CO>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([CH3:14])([CH3:13])[C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 24777892Methyl 2-(3-bromophenyl)-2-methylpropanoate

Product 1

HCID 128051282-(3-Bromophenyl)-2-methylpropanoic 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 the 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
  6. customto afford the acid

Sources & evidence

ORD record
ord-7149c62e39894887a9aa45926a305dac
Source dataset
uspto-grants-2008_03
Patent number
US07342024B2

Reaction notes

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