1,2-Dimethoxyethane → 2,3',5-Trimethyl-1,1'-biphenyl

HRID 382122

반응식

HRID 382122 반응식
C(=O)([O-])[O-].[Na+].[Na+].CC1C=[CH:12][C:11]([CH:14]([C:20]2[CH:25]=[CH:24][C:23](C)=[CH:22][CH:21]=2)[C:15](=O)[CH:16]([CH3:18])[CH3:17])=[CH:10]C=1.[CH3:27]OCCOC.BrC1C=CC=CC=1I>CCOCC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C(O)C>[CH3:12][C:11]1[CH:10]=[CH:18][C:16]([CH3:17])=[CH:15][C:14]=1[C:20]1[CH:21]=[CH:22][CH:23]=[C:24]([CH3:27])[CH:25]=1

참가 물질

9

반응물 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 114151-Bromo-2-iodobenzeneHCID 120407443-Methyl-1,1-bis(4-methylphenyl)-2-butanone

생성물 1

HCID 110416892,3',5-Trimethyl-1,1'-biphenyl수율 79%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 962Water용매HCID 3283Diethyl Ether용매

실험 절차

An oven-dried Schlenk flask was cooled to room temperature under an argon purge, and was charged with tetrakis(triphenylphosphine)palladium (289 mg, 0.25 mmol, 5 mol %) sodium carbonate (2.86 g, 27 mmol), and 1 (1.0 g, 5.0 mmol). The flask was purged with argon and DME (50 mL), ethanol (2 mL), water (15 mL), and 2-bromoiodobenzene (0.83 mL, 6.05 mmol) were added through a rubber septem. The mixture was heated to 85° C. with stirring for 3 days. The mixture was cooled to room temperature, diluted with ether (100 mL), and poured into a separatory funnel. The layers were separated and the organic phase was washed with 1M NaOH (2×50 mL), washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel to afford 1.23 g (79%) of 2 as a colorless oil.

후처리

  1. custompurge
  2. additionwere added through a rubber septem
  3. temperatureThe mixture was heated to 85° C.
  4. temperatureThe mixture was cooled to room temperature
  5. additionpoured into a separatory funnel
  6. customThe layers were separated
  7. washthe organic phase was washed with 1M NaOH (2×50 mL)
  8. washwashed with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customThe crude material was purified by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-62f12661d3664b1a8edd386db630f7ba
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06307087B1

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