Water → 3-Bromo-4-nitrophthalide

HRID 1443204Notes

Reaction equation

HRID 1443204 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][O:7][C:8]2=[O:9])([O-:3])=[O:2].[Br:14]N1C(=O)CCC1=O.O>C1(C(F)(F)F)C=CC=CC=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:14][CH:6]1[C:5]2[C:10](=[CH:11][CH:12]=[CH:13][C:4]=2[N+:1]([O-:3])=[O:2])[C:8](=[O:9])[O:7]1

Participants

6

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 12116924-Nitrophthalide

Product 1

HCID 179850383-Bromo-4-nitrophthalideYield 93.6%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 7368(Trifluoromethyl)benzeneSolvent

Procedure

5.37 g of 4-nitrophthalide (Tetrahedron Lett. (2001), 42, pp. 1647-50), 8.04 g of N-bromosuccinimide and 196 mg of benzoyl peroxide are refluxed in 80 ml of benzotrifluoride and heated by exposure to light until the reaction is completed. It is added to water, extracted with dichloromethane, washed several times with water, dried, and the solvent is removed in a vacuum. 7.24 g of 3-bromo-4-nitro-phthalide is obtained as a solid.

Workup

  1. temperatureheated by exposure to light until the reaction
  2. extractionextracted with dichloromethane
  3. washwashed several times with water
  4. customdried
  5. customthe solvent is removed in a vacuum

Sources & evidence

ORD record
ord-6f22f793fcf645e4b59562b0dbc225a9
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

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