N-(hydroxymethyl)phthalimide → HCID 53328541, compound
Reaction equation
O[CH2:2][N:3]1[C:7](=[O:8])[C:6]2=[CH:9][CH:10]=[CH:11][CH:12]=[C:5]2[C:4]1=[O:13].[Br:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:16]=1[CH3:24]>OS(C(F)(F)F)(=O)=O>[Br:14][C:15]1[C:16]([CH3:24])=[CH:17][C:18]([N+:21]([O-:23])=[O:22])=[CH:19][C:20]=1[CH2:2][N:3]1[C:7](=[O:8])[C:6]2[C:5](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:4]1=[O:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
N-(Hydroxymethyl)phtalimide (2.36 g, 13.3 mmol) was dissolved in 20 mL of triflic acid at 0° C. The mixture was stirred for 20 minutes and then 2-bromo-5-nitrotoluene (2.88 g, 1 eq) was added. This solution was allowed to warm to room temperature and was stirred for 18 h. The mixture was poured slowly into 300 mL of ice-cold water. The aqueous layer was extracted with DCM. The combined organic layers were washed with 100 mL of water, dried over Na2SO4, filtered and evaporated to yield expected compound as a white solid (4.71 g, 94% yield).