Sodium Hydroxide → 6-Fluoro-4-methoxy-biphenyl-3-carboxylic acid

HRID 457978Notes

Reaction equation

HRID 457978 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]([F:13])=[CH:9][C:10]=1[O:11][CH3:12])=[O:4].[OH-].[Na+]>O1CCOCC1>[F:13][C:8]1[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[C:10]([O:11][CH3:12])[CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 220934916-Fluoro-4-methoxy-biphenyl-3-carboxylic acid methyl ester

Product 1

HCID 184681996-Fluoro-4-methoxy-biphenyl-3-carboxylic acidYield 97.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirring solution of 6-fluoro-4-methoxy-biphenyl-3-carboxylic acid methyl ester (0.5 g, 2.3 mmol) in dioxane (8 mL, 0.3 M) was added 2N NaOH (6.0 mL, 12 mmol). After one hour at room temperature, the reaction mixture was concentrated, and 2N HCl was added. The aqueous layer was diluted with ether. The organic layer was separated, dried over Na2SO41 filtered and concentrated to afford a 6-fluoro-4-methoxy-biphenyl-3-carboxylic acid (0.55 g, 96%) as a pale yellow powder: Rf 0.18 (5% methanol in dichloromethane); 1H NMR (CDCl3, 300 MHz) δ 8.35 (d, J=9.0 Hz, 1 H), 7.55–7.52 (m, 2 H), 7.48–7.38 (m, 3 H), 6.89 (d, J=11.7 Hz, 1H), 4.12 (s, 3H).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. addition2N HCl was added
  3. additionThe aqueous layer was diluted with ether
  4. customThe organic layer was separated
  5. customdried over Na2SO41
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b0c126bb088642e4bad0d0d0f62bb2cb
Source dataset
uspto-grants-2007_03
Patent number
US07189749B2

Reaction notes

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