Sodium Carbonate → Methyl 2-(4-fluorophenyl)-4-methylbenzoate

HRID 1251864Notes

Reaction equation

HRID 1251864 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4](OS(C(F)(F)F)(=O)=O)[CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[F:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1.[Cl-].[Li+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O)C>[F:26][C:27]1[CH:32]=[CH:31][C:30]([C:4]2[CH:3]=[C:2]([CH3:1])[CH:11]=[CH:10][C:5]=2[C:6]([O:8][CH3:9])=[O:7])=[CH:29][CH:28]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 433294Lithium ChlorideHCID 18474576Methyl 2-trifluoromethylsulfonyloxy-4-methylbenzoate

Product 1

HCID 18474522Methyl 2-(4-fluorophenyl)-4-methylbenzoateYield 99%

Reagents, catalysts & solvents 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Tetrakis(triphenylphosphine) palladium (9 g; 7.8 mmol) and ethanol (780 ml) was added to a suspension of methyl 4-methyl-2-trifluoromethanesulphonyloxybenzoate (58 g; 0.195 mol), 2M aqueous solution of sodium carbonate (250 ml; 0.5 mol), 4-fluorophenylboronic acid (30 g ; 0.214 mol) and lithium chloride (16.5 g ; 0.39 mol) in toluene (1.65 ml), under an argon atmosphere, The mixture was refluxed for 4 hours, diluted with ethyl acetate (1 l) and washed with aqueous sodium hydroxide solution 1N (1 l). The organic phase was evaporated and the residue purified by flash column chromatography using ethyl acetatelpetroleum ether (95:5) to give methyl 2-(4-fluorophenyl)-4-methylbenzoate (46.8 g; 99%).

Workup

  1. temperatureThe mixture was refluxed for 4 hours
  2. washwashed with aqueous sodium hydroxide solution 1N (1 l)
  3. customThe organic phase was evaporated
  4. customthe residue purified by flash column chromatography

Sources & evidence

ORD record
ord-4f4e310c66f74ef989de0ec00154098b
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

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