4-Chloro-2-(propan-2-yl)-1H-indene → 4-(3,5-Dimethylphenyl)-2-isopropylindene

HRID 842468노트

반응식

HRID 842468 반응식
Cl[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH:11]([CH3:13])[CH3:12])[CH2:6]2.[CH3:14][C:15]1[CH:16]=[C:17]([Mg]Br)[CH:18]=[C:19]([CH3:21])[CH:20]=1>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>[CH3:14][C:15]1[CH:16]=[C:17]([C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2[CH:4]=[C:5]([CH:11]([CH3:13])[CH3:12])[CH2:6]3)[CH:18]=[C:19]([CH3:21])[CH:20]=1

참가 물질

5

반응물 2

HCID 219183974-Chloro-2-(propan-2-yl)-1H-indeneHCID 178425074HCID 178425074, 화합물

생성물 1

HCID 220230144-(3,5-Dimethylphenyl)-2-isopropylindene

시약·촉매·용매 2

HCID 178418751HCID 178418751, 화합물촉매HCID 3283Diethyl Ether용매2회

실험 절차

4-chloro-2-isopropylindene (10 g, 54 mmol) and NiCl2(PPh3)2 (1.8 g, 2.8 mmol) were dissolved in 150 mL of Et2O. 3,5-Dimethylphenylmagnesium bromide (54 mmol) as a Et2O solution was added under vigorous stirring 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 5.5 g (39%).

후처리

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

출처 및 근거

ORD 기록
ord-8d5c233fa6134ff6a95187f483718c0d
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06376409B1

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