Potassium Carbonate → 3,4'-Dimethoxybiphenyl

HRID 1943533노트

반응식

HRID 1943533 반응식
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

참가 물질

6

반응물 2

HCID 11430Potassium CarbonateHCID 696764-Iodoanisole

생성물 1

HCID 6118463,4'-Dimethoxybiphenyl수율 185.7%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 74236Tetrabutylammonium Bromide촉매HCID 86587398Ethanol toluene water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a0be07a526d64b44984dc0ef4339204c
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394468B2

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