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

HRID 1987461Notes

Reaction equation

HRID 1987461 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-ea764ad10b05443e9b2cf93351f1b8d5
Source dataset
uspto-grants-2009_06
Patent number
US07550544B2

Reaction notes

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