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

HRID 2228007Notes

Reaction equation

HRID 2228007 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.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.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 178418397HCID 178418397, compoundCatalystHCID 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 argon atmosphere. The mixture was refluxed for 4 hours, diluted with ethyl acetate (1 l), washed with aqueous sodium hydroxide solution 1N (1 l). The organic phase was evaporated and the residue purified by flash chromatography (ethyl acetate/petroleum 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 chromatography (ethyl acetate/petroleum ether: 95/5)

Sources & evidence

ORD record
ord-835291671749498482473575b00e57e1
Source dataset
uspto-grants-2002_07
Patent number
US06414145B1

Reaction notes

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