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

HRID 2220624노트

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HRID 2220624 반응식
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

참가 물질

9

반응물 5

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

생성물 1

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

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 887Methanol용매HCID 962Water용매

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온도
75 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-fccf88990ea948739379ddcb70bffc2c
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07417169B2

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