Sodium Carbonate → [1,1'-Biphenyl]-4-carboxylic acid, 4'-fluoro-2-hydroxy-, methyl ester

HRID 494193Notes

Reaction equation

HRID 494193 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[OH:12].[F:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=2[OH:12])=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 6425184Methyl 4-Bromo-3-hydroxybenzoate

Product 1

HCID 69037981[1,1'-Biphenyl]-4-carboxylic acid, 4'-fluoro-2-hydroxy-, methyl ester

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21863594Toluene ethanolSolvent

Procedure

Methyl 4-bromo-3-hydroxybenzoate (2.1 g, 9.0 mmol), 4-fluorophenyl-boronic acid (2.52 g, 18 mmol), tetrakis(triphenylphosphine)palladium (0.52 g, 0.45 mmol), and 2M aqueous sodium carbonate solution (11 ml) in ethanol/toluene (1:5, 30 ml) were heated at reflux overnight. After cooling the solvent was removed in vacuo and the residue dissolved in EtOAc then washed with sat. aq. sodium bicarbonate and dried over MgSO4. The crude product was purified by column chromatography eluting with 1% MeOH/DCM giving the title compound as a solid (1.9 g). MS(ES): MH+ 247, M-H+ 245.

Workup

  1. temperatureat reflux overnight
  2. temperatureAfter cooling the solvent
  3. customwas removed in vacuo
  4. dissolutionthe residue dissolved in EtOAc
  5. washthen washed with sat. aq. sodium bicarbonate
  6. dry with materialdried over MgSO4
  7. customThe crude product was purified by column chromatography
  8. washeluting with 1% MeOH/DCM giving the title compound as a solid (1.9 g)

Sources & evidence

ORD record
ord-23c4e1fb330c4bccb6556634d2a252af
Source dataset
uspto-grants-2009_05
Patent number
US07538121B2

Reaction notes

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