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

HRID 2229565Notes

Reaction equation

HRID 2229565 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 Na2SO4, 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, 1H), 7.55-7.52 (m, 2H), 7.48-7.38 (m, 3H), 6.89 (d, J=11.7 Hz, 1H), 4.12 (s, 3H).

Workup

  1. customAfter one'hour at room temperature
  2. concentrationthe reaction mixture was concentrated
  3. addition2N HCl was added
  4. additionThe aqueous layer was diluted with ether
  5. customThe organic layer was separated
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d6003dd9e0a94661a2228d60d4c5dee4
Source dataset
uspto-grants-2002_07
Patent number
US06420426B1

Reaction notes

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