4-Chloro-2-methyl-1H-indene → 4-(3',5'-Di-t-butylphenyl)-2-methylindene

HRID 842460노트

반응식

HRID 842460 반응식
Cl[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:11])[CH2:6]2.[C:12]([C:16]1[CH:17]=[C:18]([Mg]Br)[CH:19]=[C:20]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:21]=1)([CH3:15])([CH3:14])[CH3:13]>CCOCC.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>[C:12]([C:16]1[CH:17]=[C:18]([C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2[CH:4]=[C:5]([CH3:11])[CH2:6]3)[CH:19]=[C:20]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:21]=1)([CH3:15])([CH3:14])[CH3:13]

참가 물질

5

반응물 2

HCID 120107424-Chloro-2-methyl-1H-indeneHCID 178441125HCID 178441125, 화합물

생성물 1

HCID 120107434-(3',5'-Di-t-butylphenyl)-2-methylindene

시약·촉매·용매 2

HCID 178418751HCID 178418751, 화합물촉매HCID 3283Diethyl Ether용매2회

실험 절차

4-Chloro-2-methylindene (6.1 g, 37 mmol) and NiCl2(PPh3)2 (1.8 g, 2.8 mmol) were dissolved in 150 mL of Et2O. 3,5-Di-t-butylphenylmagnesium bromide (10 g, 37 mmol) as a Et2O solution was added to the solution and the reaction was stirred overnight at room temperature. After overnight stirring, the reaction was slowly quenched with H2O to neutralize unreacted Grignard. The solution was subsequently treated with 100 mL of 10% HCl(aq), neutralized with saturated sodium bicarbonate aqueous solution. The 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 was 4.6 g (40%).

후처리

  1. stirringAfter overnight stirring
  2. customthe reaction was slowly quenched with H2O
  3. additionThe solution was subsequently treated with 100 mL of 10% HCl(aq)
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. customthe solvent was removed by rotary evaporation
  6. washeluted with hexane

출처 및 근거

ORD 기록
ord-7dbc63b983324b8da8d1d03478b065e9
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06376409B1

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