Sodium Hydroxide → 4-(2,4-difluorophenyl)benzoic Acid

HRID 1174952Notes

Reaction equation

HRID 1174952 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=2[F:18])=[CH:7][CH:6]=1)=[O:4].[OH-].[Na+]>O>[F:18][C:12]1[CH:13]=[C:14]([F:17])[CH:15]=[CH:16][C:11]=1[C:8]1[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57771752Methyl 4-(2,4-difluorophenyl)benzoate

Product 1

HCID 27582644-(2,4-difluorophenyl)benzoic AcidYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

Dissolve 2′,4′-difluoro-biphenyl-4-carboxylic acid methyl ester (0.426 g, 1.716 mmol) in THP (5 mL) and add a solution of NaOH (0.164 g, 4.12 mmol) in water (5.0 mL). Stir the mixture for 3 d at 40° C. Concentrate in vacuo to remove THF, add 1.0M HCl until pH 2, adsorb the mixture onto silica gel, and subject the mixture to flash column chromatography (40 g column, eluting with 50% ethyl acetate/n-hexane to 100% ethyl acetate) to yield the desired-product (0.373 g, 93%). mass spectrum (m/e): 233.3 (M−1).

Workup

  1. concentrationConcentrate in vacuo
  2. customto remove THF
  3. additionadd 1.0M HCl until pH 2, adsorb the mixture onto silica gel
  4. washto flash column chromatography (40 g column, eluting with 50% ethyl acetate/n-hexane to 100% ethyl acetate)

Sources & evidence

ORD record
ord-bcd4176684624e22a9c75329def91b96
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

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