Pyridine → 1-(3-Bromo-1-propyn-1-yl)-3-fluorobenzene
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][CH2:10]O)[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[Br:18]P(Br)Br>C(OCC)C>[Br:18][CH2:10][C:9]#[C:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -2.5 °C
Procedure
3-(3-Fluoro-phenyl)-prop-2-yn-1-ol (0.750 g, 0.005 mol) was taken in diethyl ether (10 ml) containing catalytic amount of pyridine (0.05 ml). The reaction mixture was then cooled to −5-0° C. Tribromo phosphine (0.26 ml, 0.003 mol) was added slowly at −5-0° C. and stirred at the same temperature for 3 hrs. The reaction mixture was quenched with saturated NaHCO3 solution and extracted with ethyl acetate. The organic layer was washed with saturated brine solution, dried over Na2SO4, and evaporated under vacuum to get 1-(3-bromo-prop-1-ynyl)-3-fluoro benzene (0.805 gm, 76%).
Workup
- customThe reaction mixture was quenched with saturated NaHCO3 solution
- extractionextracted with ethyl acetate
- washThe organic layer was washed with saturated brine solution
- dry with materialdried over Na2SO4
- customevaporated under vacuum
Sources & evidence
- ORD record
- ord-7cb7531f5cea427e912f4b95c07764cd
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08252797B2
Reaction notes
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