HCID 12018441, compound → 2,4-Dichloro-1-ethynylbenzene
Reaction equation
Br[C:2](Br)=[CH:3][C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1[Cl:11].C([Li])CCC>C1COCC1>[Cl:11][C:5]1[CH:6]=[C:7]([Cl:10])[CH:8]=[CH:9][C:4]=1[C:3]#[CH:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
A solution of 1,1-dibromo-2-(2,4-dichlorophenyl)ethene (14 g, 42.4 mmol) in THF (100 ml) at −78° C. under nitrogen was treated with butyllithium (1.6 M solution in hexane, 28 ml, 44.8 mmol). after being stirred for 1 hour at −78° C, the reaction mixture was warmed to room temperature and stirred for another hour. The reaction was quenched with water and the product was extracted with hexanes. The extract was dried over MgSO4, filtrated and concentrated in vacuo to give the product. (Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 3769)
Workup
- temperaturethe reaction mixture was warmed to room temperature
- stirringstirred for another hour
- customThe reaction was quenched with water
- extractionthe product was extracted with hexanes
- dry with materialThe extract was dried over MgSO4
- filtrationfiltrated
- concentrationconcentrated in vacuo
- customto give the product
Sources & evidence
- ORD record
- ord-f96ddd35dd0c48529e1aea558c55913b
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06352990B1
Reaction notes
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