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

HRID 1022386Notes

Reaction equation

HRID 1022386 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) is added 1N aqueous sodium hydroxide (47.4 ml) and the reaction mixture is stirred at room temperature for 18 hours. The mixture is 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 is 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-c592fdb70c31478ba7cdc272fb3dffaa
Source dataset
uspto-grants-2014_05
Patent number
US08722578B2

Reaction notes

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