Sodium Carbonate → Methyl 6-fluoro-2'-hydroxy[1,1'-biphenyl]-3-carboxylate

HRID 2053052Notes

Reaction equation

HRID 2053052 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([F:10])=[C:6](Br)[CH:5]=1.CC1(C)C(C)(C)OB([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[OH:27])O1.C(=O)([O-])[O-].[Na+].[Na+].N1C=CN=N1>C(OCC)(=O)C.O.C(O)CC.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([F:10])=[C:6]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[OH:27])[CH:5]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 27346222-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 7018022Methyl 3-bromo-4-fluorobenzoateHCID 178418936HCID 178418936, compound

Product 1

HCID 53218663Methyl 6-fluoro-2'-hydroxy[1,1'-biphenyl]-3-carboxylate

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 10311-PropanolSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2 g (8.45 mmol) of methyl-3-bromo-4-fluorobenzoate in 28 Ml of toluene at RT was added 0.49 g (0.42 mmol) of tetrakis(triphenyl phosphine)palladium(0), 1.95 g (8.9 mmol) of 2-(4,4,5,5,-tetramethyl-1.3.2-dioxaborolan-2-yl)phenol, 5.1 Ml (10.15 mmol) of 2M aqueous sodium carbonate solution and 14 Ml of n-propanol. The reaction mixture was heated at reflux for 18 h. The reaction mixture was cooled and diluted with ethyl acetate and water. The organic fraction was separated and washed with saturated NaCl solution (brine), dried over MgSO4, filtered and the filtrate was concentrated to an oil which was purified by chromatography (silica, 90:1, 30:1 successively CH2Cl2:acetone) to give the title compound. Mass Spectrum (ESI) m/e (M+1): 247.0.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 18 h
  3. temperatureThe reaction mixture was cooled
  4. customThe organic fraction was separated
  5. washwashed with saturated NaCl solution (brine)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated to an oil which
  9. customwas purified by chromatography (silica, 90:1, 30:1 successively CH2Cl2

Sources & evidence

ORD record
ord-9aa6d8e99660413f8a7d1a6216a31d26
Source dataset
uspto-grants-2008_02
Patent number
US07326726B2

Reaction notes

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