1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-(Azidomethyl)-3-methoxy-5-nitrobenzene

HRID 2071011Notes

Reaction equation

HRID 2071011 reaction equation
C1(P([N:15]=[N+:16]=[N-:17])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2.[CH3:29][O:30][C:31]1[CH:32]=[C:33]([CH2:40]O)[CH:34]=[C:35]([N+:37]([O-:39])=[O:38])[CH:36]=1>C1(C)C=CC=CC=1>[N:15]([CH2:40][C:33]1[CH:34]=[C:35]([N+:37]([O-:39])=[O:38])[CH:36]=[C:31]([O:30][CH3:29])[CH:32]=1)=[N+:16]=[N-:17]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 45091344(3-Methoxy-5-nitrophenyl)methanol

Product 1

HCID 811549411-(Azidomethyl)-3-methoxy-5-nitrobenzeneYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Diphenylphosphoryl azide (0.316 ml, 0.4 g, 1.46 ml, 1.1 eq) and 1,8-Diazabicyclo(5.4.0)undec-7-ene (0.219 ml, 0.22 g, 1.46 mmol, 1.1 eq) were added to a stirred solution of (3-methoxy-5-nitrophenyl)methanol in 10 ml anhydrous toluene under Ar. After stirring overnight the solvent was removed in vacuo. Purification via flash chromatography yielded 0.278 g (1.34 mmol, 100% yield) of 1-(azidomethyl)-3-methoxy-5-nitrobenzene.

Workup

  1. customwas removed in vacuo
  2. customPurification via flash chromatography

Sources & evidence

ORD record
ord-08aca6ce77194f49b4ee8bf2f53bad4e
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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