Tetrahydrofuran → HCID 59511923, compound

HRID 1157945Notes

Reaction equation

HRID 1157945 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:6]=1[Br:14])=[N+]=[N-].C1COCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O>[Br:14][C:6]1[CH:7]=[CH:8][C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:5]=1[CH2:4][NH2:1]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 59511835Benzene, 2-(azidomethyl)-1-bromo-4-nitro-

Product 1

HCID 59511923HCID 59511923, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 2-azidomethyl-1-bromo-4-nitrobenzene (6.57 g) and THF (50 mL) there was added triphenylphosphine (7.05 g) at 0° C. under a nitrogen atmosphere. The mixture was stirred at 0° C. for 1 hour and then at room temperature for 2 hours, after which water (10 mL) was added and the mixture was heated to reflux for 15 hours. The solvent in the mixture was distilled off under reduced pressure and the residue was purified by NH silica gel column chromatography (ethyl acetate-heptane mixture) to obtain the target compound (5.64 g) as a colorless solid.

Workup

  1. waitat room temperature for 2 hours
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 15 hours
  4. distillationThe solvent in the mixture was distilled off under reduced pressure
  5. customthe residue was purified by NH silica gel column chromatography (ethyl acetate-heptane mixture)

Sources & evidence

ORD record
ord-f4a93e35107043909174e19546bd1416
Source dataset
uspto-grants-2010_10
Patent number
US07807690B2

Reaction notes

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