Sodium Hydroxide → 2-(4-(Methoxycarbonyl)phenyl)-2,2-difluoroacetic acid

HRID 913249

Reaction equation

HRID 913249 reaction equation
[F:1][C:2]([C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=1)([F:7])[C:3]([O:5]C)=[O:4].[OH-].[Na+]>C1COCC1>[F:1][C:2]([F:7])([C:8]1[CH:9]=[CH:10][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:16][CH:17]=1)[C:3]([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57541237Methyl 4-(1,1-difluoro-2-methoxy-2-oxoethyl)benzoate

Product 1

HCID 575412392-(4-(Methoxycarbonyl)phenyl)-2,2-difluoroacetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-(1,1-difluoro-2-methoxy-2-oxoethyl)benzoate (1.0 g, 4.1 mmol) in THF (20 mL) was added sodium hydroxide (4.1 mmol, 4.1 mL of a 1M solution) dropwise at ambient temperature. The resulting solution was stirred for 16 hours. The reaction was partitioned between 1M HCl and ethyl acetate. The organics were dried over sodium sulfate, filtered and evaporated to give difluoro[4-(methoxycarbonyl)phenyl]acetic acid as a white solid. 1H NMR (CDCl3) δ 8.12 (d, J=8.5 Hz, 2H), 7.71 (d, J=8.21 Hz, 2H), 3.94 (s, 3H), 3.0 (bs, 1H); ESIMS calcd 231.0 (M++H), found 231.0 (M++H).

Workup

  1. customThe reaction was partitioned between 1M HCl and ethyl acetate
  2. dry with materialThe organics were dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-974bb4ff8bc54af584701d18b054ce42
Source dataset
uspto-grants-2011_09
Patent number
US08026260B2

Linked notes

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