4-(3,3-Dibromo-2-propenyl)anisole → 1-Methoxy-4-(prop-2-yn-1-yl)benzene
Reaction equation
Br[C:2](Br)=[CH:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1.[Li]CCCC>C1COCC1>[CH2:4]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)[C:3]#[CH:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of Compound 75 (478 mg, 1.56 mmol) in THF (6 ml) was added n-BuLi (1.94 ml, 3.28 mmol), at -78° C. under N2, then warmed up to 0° C., and stirred for 5 h. The mixture was quenched by the addition of NH4Cl aq., and extracted with Et2O. The combined organic layers were dried over MgSO4, filtered, and concentrated. This was purified by SiO2 chromatography to give Compound 76 (213 mg, 94%) as a colorless oil.
Workup
- customThe mixture was quenched by the addition of NH4Cl aq.
- extractionextracted with Et2O
- dry with materialThe combined organic layers were dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThis was purified by SiO2 chromatography
Sources & evidence
- ORD record
- ord-e4bd69b82ce34921b01b5faacddf1ae4
- Source dataset
- uspto-grants-1998_08
- Patent number
- US05789423
Reaction notes
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