Triphenylphosphine → 4-Bromobenzylamine
Reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([CH2:6][N:7]=[N+]=[N-])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CO>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of azide 55 (0.75 g, 3.54 mmol) in anhydrous methanol (10 mL) was added triphenylphosphine (1.39 g, 5.31 mmol) and the mixture was heated under reflux for 1.5 hours. The reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. The residue was purified by flash column chromatography on silica gel (acetone-hexane) to yield product 56 in 63% yield (0.41 g).
Workup
- temperaturethe mixture was heated
- temperatureunder reflux for 1.5 hours
- customthe solvent was removed under reduced pressure
- customThe residue was purified by flash column chromatography on silica gel (acetone-hexane)
Sources & evidence
- ORD record
- ord-64ec4365084a4e599d116e72968b65f5
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09102622B2
Reaction notes
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