Dimethyl Sulfoxide → Methyl 4-bromo-2,6-diMethylbenzoate

HRID 2220624Notes

Reaction equation

HRID 2220624 reaction equation
FC(F)(F)S(O[C:7]1[C:12]([CH3:13])=[CH:11][C:10]([Br:14])=[CH:9][C:8]=1[CH3:15])(=O)=O.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.CS(C)=O.[C:58]([O:61][CH2:62]C)(=[O:60])C>CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[Br:14][C:10]1[CH:11]=[C:12]([CH3:13])[C:7]([C:58]([O:61][CH3:62])=[O:60])=[C:8]([CH3:15])[CH:9]=1

Participants

9

Reactant 5

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 812191,3-Bis(diphenylphosphino)propaneHCID 231343334-Bromo-2,6-dimethylphenyl trifluoromethanesulfonate

Product 1

HCID 23134395Methyl 4-bromo-2,6-diMethylbenzoate

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 4-bromo-2,6-dimethylphenyl trifluoromethanesulfonate (1.439 g), palladium acetate (0.049 g), 1,3-bis(diphenylphosphino)propane (0.089 g) and triethylamine (1.336 mL) in methanol (10 mL)/dimethylsulfoxide (15 mL) was stirred at 75° C. overnight under an atmosphere of carbon monoxide. Water and ethyl acetate were added to the reaction mixture. The organic layer was separated, washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/5) to afford the title compound (0.435 g).

Workup

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/5)

Sources & evidence

ORD record
ord-fccf88990ea948739379ddcb70bffc2c
Source dataset
uspto-grants-2008_08
Patent number
US07417169B2

Reaction notes

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