Water → 3-Bromo-4-nitrophthalide

HRID 2118081Notes

Reaction equation

HRID 2118081 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 heated in 80 ml of benzotrifluoride under reflux and with 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. temperatureunder reflux and with 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-4b7c78f161f2427ea4c2dd8b0f18c4ed
Source dataset
uspto-grants-2008_10
Patent number
US07442794B2

Reaction notes

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