1,8-Diazabicyclo(5.4.0)undec-7-ene → 1-(Azidomethyl)-3-bromo-2-methoxybenzene

Reaction equation

P([N:17]=[N+:18]=[N-:19])(=O)(OC1C=CC=CC=1)OC1C=CC=CC=1.N12CCCN=C1CCCCC2.[Br:31][C:32]1[C:33]([O:40][CH3:41])=[C:34]([CH2:38]O)[CH:35]=[CH:36][CH:37]=1>C1(C)C=CC=CC=1>[N:17]([CH2:38][C:34]1[CH:35]=[CH:36][CH:37]=[C:32]([Br:31])[C:33]=1[O:40][CH3:41])=[N+:18]=[N-:19]

Participants

Procedure

6.00 g of diphenyl phosphorazidate and 4.1 g of 1,8-diazabicyclo[5.4.0]undec-7-ene were added to 4.0 g of 3-bromo-2-methoxy-phenyl-methanol 6 in 100 mL of toluene at 0° C. The mixture was stirred at room temperature overnight. The reaction mixture was quenched with aqueous ammonium chloride. The aqueous layer was extracted with ethyl acetate/THF. The pooled organic extracts were washed with brine and dried over magnesium sulfate. The mixture was filtered. The solvents were removed under vacuum. The residue was purified by chromatography on silica gel to give 1-azidomethyl-3-bromo-2-methoxy-benzene 7.