N-(hydroxymethyl)phthalimide → HCID 53328541, compound

HRID 1190873Notes

Reaction equation

HRID 1190873 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

HCID 8354N-(hydroxymethyl)phthalimideHCID 2516721-Bromo-2-methyl-4-nitrobenzene

Product 1

HCID 53328541HCID 53328541, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 62406Trifluoromethanesulfonic acidSolvent

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).

Workup

  1. stirringwas stirred for 18 h
  2. extractionThe aqueous layer was extracted with DCM
  3. washThe combined organic layers were washed with 100 mL of water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-16257a32f1734483b23335fe4c3f7518
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

Loading…