4-Bromo-2,5-dimethyl-1h-indene → 2,5-Dimethyl-4-phenylindene

HRID 1372538노트

반응식

HRID 1372538 반응식
Br[C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:12])[CH2:6]2.[C:13]1([Mg]Br)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(OCC)C.Cl[Ni](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:12][C:5]1[CH2:6][C:7]2[C:3]([CH:4]=1)=[C:2]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:10]([CH3:11])=[CH:9][CH:8]=2

참가 물질

5

반응물 2

HCID 231154544-Bromo-2,5-dimethyl-1h-indeneHCID 178418255HCID 178418255, 화합물

생성물 1

HCID 231154562,5-Dimethyl-4-phenylindene

시약·촉매·용매 2

HCID 178418751HCID 178418751, 화합물촉매HCID 3283Diethyl Ether용매2회

실험 절차

4-Bromo-2,5-dimethylindene (9.0 g, 40 mmol), prepared as described under I.(b) above, and NiCl2(PPh3)2 (1.8 g, 2.8 mmol) were dissolved in 300 ml of diethyl ether (Et2O). Phenylmagnesium bromide, 3.0 M in Et2O, (13.5 ml, 40 mmol) was added under vigorous stirring and the reaction stirred overnight at reflux. The resultant reaction was slowly quenched with H2O to neutralize unreacted Grignard reagent, subsequently treated with 100 ml of 10% HCl(aq), and neutralized with saturated sodium bicarbonate aqueous solution. The resultant organic layer was dried with magnesium sulfate, and the solvent was removed by rotary evaporation. The remaining residue was loaded onto a silica gel column and eluted with hexane. Yield is 1.3 g (15%).

후처리

  1. stirringthe reaction stirred overnight
  2. temperatureat reflux
  3. customThe resultant reaction
  4. customwas slowly quenched with H2O
  5. additionsubsequently treated with 100 ml of 10% HCl(aq)
  6. dry with materialThe resultant organic layer was dried with magnesium sulfate
  7. customthe solvent was removed by rotary evaporation
  8. washeluted with hexane

출처 및 근거

ORD 기록
ord-521cbc1d20c3480697c10f38a8226be0
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07157591B2

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