Triphenylphosphine → 4-Bromobenzylamine

HRID 511992Notes

Reaction equation

HRID 511992 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]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 109875654-Bromobenzyl azide

Product 1

HCID 775714-BromobenzylamineYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. customthe solvent was removed under reduced pressure
  4. 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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