Phosphorus tribromide → (E)-3-[3-(3-thienyl)phenyl]-2-propenyl bromide
Reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8]([CH:16]=[CH:17][CH:18]=2)/[CH:9]=[CH:10]/[C:11](OCC)=O)=[CH:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].P(Br)(Br)[Br:26]>>[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8](/[CH:9]=[CH:10]/[CH2:11][Br:26])[CH:16]=[CH:17][CH:18]=2)=[CH:2]1Participants
Procedure
1.0 g of the resulting ester compound was reduced in a customary manner with lithium aluminum hydride, and then brominated by phosphorus tribromide. 0.7 g of (E)-3-[3-(3-thienyl)phenyl]-2-propenyl bromide obtained thus was dissolved in 10 ml of dimethylformamide, and 0.6 g of potassium phthalimide was added. The mixture was stirred overnight at room temperature, and the solution was worked up in a customary manner to give (E)-N-[3-[3-(3-thienyl)phenyl]-2-propenyl] phthalimide. 0.7 g of the resulting phthalimide compound was dissolved in a mixture (3 ml) of tetrahydrofuran and ethanol (1:1), and 0.5 ml of hydrazine hydrate was added. The mixture was stirred at room temperature for 1 hour, and then worked up in a customary manner to give 0.42 g of the captioned compound.
Sources & evidence
- ORD record
- ord-58310e5f689e43c2b9a24d043a02e173
- Source dataset
- uspto-grants-1995_08
- Patent number
- US05439932
Reaction notes
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