N-bromobutanimide → HCID 18996368, compound

HRID 374891Notes

Reaction equation

HRID 374891 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:5](=[CH:11][CH:12]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7].BrN1C(=[O:24])CCC1=O>[W].C(Cl)(Cl)(Cl)Cl>[CH:1]([C:2]1[CH:3]=[C:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:5](=[CH:11][CH:12]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])=[O:24]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 10911539HCID 10911539, compound

Product 1

HCID 18996368HCID 18996368, compound

Reagents, catalysts & solvents 2

HCID 23964TungstenCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of one equivalent of diethyl 4-methylphthalate, two equivalents of N-bromosuccinimide and carbon tetrachloride is irradiated with a 500 W tungsten lamp for three hours. The mixture is filtered and the solution is shaken with excess sodium carbonate solution. Evaporation of the organic phase gives diethyl 4-formylphthalate. This aldehyde is combined with excess nitroethane, toluene and a catalytic amount of benzyl amine. The mixture is heated on a steam bath for 48 hours and evaporated in vacuo to give diethy 4-(2-nitropropen-1-yl)phthalate.

Workup

  1. filtrationThe mixture is filtered
  2. customEvaporation of the organic phase

Sources & evidence

ORD record
ord-edb4253312d345b8bf471c67127223cc
Source dataset
uspto-grants-1996_01
Patent number
US05482971

Reaction notes

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