Dimethyl Sulfoxide → Methyl 4-bromo-2-isopropylbenzoate

HRID 2220606Notes

Reaction equation

HRID 2220606 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][C:8]=1[CH:14]([CH3:16])[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:59]([O:62][CH2:63]C)(=[O:61])C>CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[Br:13][C:10]1[CH:11]=[CH:12][C:7]([C:59]([O:62][CH3:63])=[O:61])=[C:8]([CH:14]([CH3:16])[CH3:15])[CH:9]=1

Participants

9

Reactant 5

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 812191,3-Bis(diphenylphosphino)propaneHCID 23134099HCID 23134099, compound

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 trifluoromethanesulfonate (0.705 g), palladium acetate (0.0228 g), 1,3-bis-(diphenylphosphino)propane (0.0419 g) and triethylamine (0.628 mL) in methanol (6 mL)/dimethylsulfoxide (9 mL) was stirred at 55° 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: diethyl ether/n-hexane=1/10) to afford methyl 4-bromo-2-isopropylbenzoate (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-8d42d539cd7242918d06ef6ac515b571
Source dataset
uspto-grants-2008_08
Patent number
US07417169B2

Reaction notes

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