Sodium Hydroxide → 2-(5-Bromo-4-fluoro-2-methylphenyl)acetic acid

HRID 1962374Notes

Reaction equation

HRID 1962374 reaction equation
C[O:2][C:3](=[O:14])[CH2:4][C:5]1[CH:10]=[C:9]([Br:11])[C:8]([F:12])=[CH:7][C:6]=1[CH3:13].[OH-].[Na+]>CO>[Br:11][C:9]1[C:8]([F:12])=[CH:7][C:6]([CH3:13])=[C:5]([CH2:4][C:3]([OH:14])=[O:2])[CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59614585(5-Bromo-4-fluoro-2-methyl-phenyl)-acetic acid methyl ester

Product 1

HCID 596146012-(5-Bromo-4-fluoro-2-methylphenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (5-bromo-4-fluoro-2-methyl-phenyl)-acetic acid methyl ester (10.3 g) in methanol (50 ml) was added 1N aqueous sodium hydroxide (47.4 ml) and the reaction mixture was stirred at room temperature for 18 hours. The mixture was concentrated, the residue treated with 1N hydrochloric acid, the resulting precipitate filtered off, washed with ice-water and dried. Yield: 8.60 g of (5-bromo-4-fluoro-2-methyl-phenyl)-acetic acid as a solid, mp: 100-101° C.

Workup

  1. concentrationThe mixture was concentrated
  2. additionthe residue treated with 1N hydrochloric acid
  3. filtrationthe resulting precipitate filtered off
  4. washwashed with ice-water
  5. customdried

Sources & evidence

ORD record
ord-de90db20102548c4abaeab3708d10805
Source dataset
uspto-grants-2013_04
Patent number
US08415369B2

Reaction notes

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