Potassium Carbonate → 3,4'-Dimethoxybiphenyl

HRID 1943533

反応式

HRID 1943533 の反応式
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[C:10](=[O:13])([O-])[O-].[K+].[K+]>[Pd].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.C(O)C.O>[CH3:9][O:8][C:5]1[CH:4]=[C:3]([C:2]2[CH:7]=[CH:6][C:5]([O:13][CH3:10])=[CH:4][CH:3]=2)[CH:2]=[CH:7][CH:6]=1

参加物

6

反応物 2

HCID 11430Potassium CarbonateHCID 696764-Iodoanisole

生成物 1

HCID 6118463,4'-Dimethoxybiphenyl収率 185.7%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 74236Tetrabutylammonium Bromide触媒HCID 86587398Ethanol toluene water溶媒

実験手順

A mixture of a mixed solvent (toluene/ethanol/water=1.5/1.5/1; 900 ml), the compound (T-2) (48.6 g, 319.6 mmol), 1-iodo-4-methoxybenzene (68.0 g, 290.6 mmol), 5% palladium on carbon (3.40 g), potassium carbonate (60.2 g, 435.9 mmol) and tetrabutylammonium bromide (23.4 g, 72.7 mmol) was refluxed with stirring for 15 hours under an atmosphere of nitrogen. The resulting reaction mixture was extracted with toluene (400 mL) three times, and the organic layers were washed with water. After the organic layer had been dried over anhydrous magnesium sulfate, the organic solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent: toluene), and then by recrystallization from a mixed solvent of heptane, methanol and ethyl acetate to give colorless crystals (57.8 g) of 3,4′-dimethoxybiphenyl (T-3).

後処理

  1. customThe resulting reaction mixture
  2. extractionwas extracted with toluene (400 mL) three times
  3. washthe organic layers were washed with water
  4. dry with materialAfter the organic layer had been dried over anhydrous magnesium sulfate
  5. distillationthe organic solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel chromatography (eluent: toluene)
  7. customby recrystallization from a mixed solvent of heptane, methanol and ethyl acetate

出典と根拠

ORDレコード
ord-a0be07a526d64b44984dc0ef4339204c
出典データセット
uspto-grants-2013_03
特許番号
US08394468B2

関連ノート

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