Dimethyl Sulfoxide → Methyl 4-bromo-2-isopropylbenzoate

HRID 30737Notes

Reaction equation

HRID 30737 reaction equation
CS(O[C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][C:7]=1[CH:13]([CH3:15])[CH3:14])(=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:56]([O:59][CH2:60]C)(=[O:58])C>CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[Br:12][C:9]1[CH:10]=[CH:11][C:6]([C:56]([O:59][CH3:60])=[O:58])=[C:7]([CH:13]([CH3:15])[CH3:14])[CH:8]=1

Participants

9

Reactant 5

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 812191,3-Bis(diphenylphosphino)propaneHCID 230907374-Bromo-2-isopropylphenyl methanesulfonate

Product 1

HCID 22171591Methyl 4-bromo-2-isopropylbenzoate

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 4-bromo-2-isopropylphenyl methanesulfonate (0.71 g), palladium acetate (0.023 g), 1,3-bis(diphenylphosphino)propane (0.042 g) and triethylamine (0.63 mL) in methanol (6 mL)/dimethylsulfoxide (9 mL) was stirred overnight at 55° C. 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: diethyl ether/n-hexane=1/10) to afford the title compound (0.355 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: diethyl ether/n-hexane=1/10)

Sources & evidence

ORD record
ord-514db7685ad04ffca226bb87392ea871
Source dataset
uspto-grants-2008_09
Patent number
US07423185B2

Reaction notes

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