Water → (4-Bromo-6-fluoro-2-methyl-1H-inden-1-yl) (9H-fluoren-9-yl)dimethylsilane

HRID 1987461노트

반응식

HRID 1987461 반응식
[Br:1][C:2]1[CH:3]=[C:4]([F:12])[CH:5]=[C:6]2[C:10]=1[CH2:9][C:8]([CH3:11])=[CH:7]2.[Li]CCCC.[CH:18]1[C:30]2[CH:29]([Si:31](Cl)([CH3:33])[CH3:32])[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]=2[CH:21]=[CH:20][CH:19]=1.O>CCOCC>[Br:1][C:2]1[CH:3]=[C:4]([F:12])[CH:5]=[C:6]2[C:10]=1[CH:9]=[C:8]([CH3:11])[CH:7]2[Si:31]([CH:29]1[C:28]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:22]2[C:30]1=[CH:18][CH:19]=[CH:20][CH:21]=2)([CH3:32])[CH3:33]

참가 물질

6

반응물 4

HCID 962WaterHCID 5648779-(Chlorodimethylsilyl)-9h-fluoreneHCID 598325417-bromo-5-fluoro-2-methyl-1H-indeneHCID 178418339Butyllithium

생성물 1

HCID 57723641(4-Bromo-6-fluoro-2-methyl-1H-inden-1-yl) (9H-fluoren-9-yl)dimethylsilane

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

To a solution of 3.41 g (15.0 mmol) of 7-bromo-5-fluoro-2-methyl-1H-indene in 80 ml of ether, 6.00 ml (15.0 mmol) of 2.5 M nBuLi in hexanes was added. The reaction mixture was stirred for 12 h at room temperature; then, this solution was added dropwise to a solution of 3.88 g (15.0 mmol) of (9H-fluoren-9-yl)chlorodimethylsilane in 80 ml of ether over 1 h at room temperature. The resulting mixture was stirred for 12 h, and then 100 ml of water was added. The organic layer was separated, dried over Na2SO4, and evaporated to dryness. The product was isolated by flash chromatography on Silica Gel 60 (40-63 um, d 30 mm, l 400 mm, eluent: hexanes). Yield 3.71 g (55%).

후처리

  1. stirringThe resulting mixture was stirred for 12 h
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness
  5. customThe product was isolated by flash chromatography on Silica Gel 60 (40-63 um, d 30 mm, l 400 mm, eluent: hexanes)

출처 및 근거

ORD 기록
ord-ea764ad10b05443e9b2cf93351f1b8d5
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07550544B2

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