Benzene, 1-bromo-3-nitro- → 1-Nitro-3-[2-(trimethylsilyl)ethynyl]-benzene
Reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[CH:3]=1.[CH3:11][Si:12]([C:15]#[CH:16])([CH3:14])[CH3:13]>[Cu]I.C(N(CC)CC)C>[CH3:11][Si:12]([C:15]#[C:16][C:2]1[CH:3]=[C:4]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:6][CH:7]=1)([CH3:14])[CH3:13]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 82.5 °C
Procedure
A mixture of 1-bromo-3-nitrobenzene (10.0 g, 49.45 mmol) and trimethylsilylacetylene (8.4 mL, 59.34 mmol) was treated with triethylamine (33 mL), giving a small amount of white precipitate. The resultant mixture was treated with dichlorobis(triphenylphonsphone)palladium II (7 mgs, 0.01 mmol) and copper (I) iodide (8.5 mgs, 0.04 mmol) and heated at 80-85° C. (oil bath temperature) for 4 hours. The resultant bright yellow mixture was allowed to cool to room temperature and the solid was removed by filtration with the aid of triethylamine (33 mL). The clear yellow solution was concentrated by evaporation and dried in vacuo at room temperature overnight to give the title product (11.11 g, 102%) as a dark brown oil. gc/mass spectroscopy indicated that the final compound was 100% pure m/e 219 (M+H)+
Workup
- customgiving a small amount of white precipitate
- temperatureto cool to room temperature
- customthe solid was removed by filtration with the aid of triethylamine (33 mL)
- concentrationThe clear yellow solution was concentrated by evaporation
- customdried in vacuo at room temperature overnight
Sources & evidence
- ORD record
- ord-e19da05ab2e446d78ef732c5fdee18d3
- Source dataset
- uspto-grants-2002_11
- Patent number
- US06476040B1
Reaction notes
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