Butyl iodide → 2-butyl-9,9-dimethyl-6,7,8,9-tetrahydro-5H-benzo-cycloheptene
Reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7]([CH3:13])([CH3:12])[C:6]=2[CH:14]=1.I[CH2:16][CH2:17][CH2:18][CH3:19]>[Cu]I.O1CCCC1>[CH2:16]([C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7]([CH3:13])([CH3:12])[C:6]=2[CH:14]=1)[CH2:17][CH2:18][CH3:19]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -15 °C
Procedure
The corresponding Grignard compound was prepared under argon from 304 mg of Mg shavings and 2.50 g of 2-bromo-9,9-dimethyl-6,7,8,9-tetrahydro-5H-benzocycloheptene in 25 ml of abs. tetrahydrofuran. After cooling to −15° C. 206 mg of CuI and 1.78 ml of 1-iodobutane were added in succession. The mixture was left to react at room temperature for 2 hours and then poured into ice/ammonium chloride solution. The solution was extracted with diethyl ether, washed with water, dried and evaporated. After filtration over SiO2 with hexane as the eluent there were obtained 2.27 g of 2-butyl-9,9-dimethyl-6,7,8,9-tetrahydro-5H-benzo-cycloheptene (contaminated with 4% regioisomers and 6% 5,5-dimethyl-6,7,8,9-tetrahydro-5H-benzocyloheptene).
Workup
- waitThe mixture was left
- customto react at room temperature for 2 hours
- extractionThe solution was extracted with diethyl ether
- washwashed with water
- customdried
- customevaporated
- filtrationAfter filtration over SiO2 with hexane as the eluent there
Sources & evidence
- ORD record
- ord-e4458d44d23a45998a1c6eb629f6ee33
- Source dataset
- uspto-grants-2003_08
- Patent number
- US06610877B1
Reaction notes
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