1H-Indene, 2-methyl- → 7-(2-bromoethyl)-2-methyl-1H-indene
Reaction equation
[CH3:1][C:2]1[CH2:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[Li]CCCC.[Br:16][CH2:17][C:18]1C=CC=C2C=1CC(C)=C2.CC1C(CC2C=CC=C3C=2CC(C)=C3)C2C(C=1)=CC=CC=2>CCOCC.C1COCC1.O>[Br:16][CH2:17][CH2:18][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[CH2:3][C:2]([CH3:1])=[CH:10]2Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
To a solution of 1.30 g (10 mmol) of 2-methyl-1H-indene in 90 ml of ether 4.0 ml of 2.5 M (10 mmol) n-BuLi in hexanes was added at 0° C. This mixture was stirred for 2 h at room temperature, and then a solution of 2.23 g (10 mmol) of 7-(bromomethyl)-2-methyl-1H-indene in 15 ml of THF was added dropwise at vigorous stirring for 10 min at −80° C. The resulting mixture was stirred for 12 h at room temperature, and then 1 ml of water was added. This mixture was evaporated to dryness, and 100 ml of water was added. The crude product was extracted with 3×50 ml of dichloromethane. The combined organic extract was dried over Na2SO4 and evaporated to dryness. The product was isolated by flash chromatography using a short column with Silica Gel 60 (40-63 um, d 60 mm, l 70 mm; eluent: hexanes. Yield 2.50 g (92%) of 2-methyl-1-[(2-methyl-1H-inden-7-yl)methyl]-1H-indene.
Workup
- stirringat vigorous stirring for 10 min at −80° C
- stirringThe resulting mixture was stirred for 12 h at room temperature
- customThis mixture was evaporated to dryness, and 100 ml of water
- additionwas added
- extractionThe crude product was extracted with 3×50 ml of dichloromethane
- extractionThe combined organic extract
- dry with materialwas dried over Na2SO4
- customevaporated to dryness
- customThe product was isolated by flash chromatography
Sources & evidence
- ORD record
- ord-95d0714034a74fc9a0631cea6f7d0f36
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08569532B2
Reaction notes
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