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

HRID 2220624ノート

反応式

HRID 2220624 の反応式
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

参加物

9

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
75 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-fccf88990ea948739379ddcb70bffc2c
出典データセット
uspto-grants-2008_08
特許番号
US07417169B2

反応ノート

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