2,5-Dinitrophenol → 1-Bromo-4-(2,5-dinitrophenyloxy)but-2-ene

HRID 50520

Reaction equation

HRID 50520 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]=1[OH:13])([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[Br:20][CH2:21][CH:22]=[CH:23][CH2:24]Br>CN1C(=O)CCC1>[Br:20][CH2:21][CH:22]=[CH:23][CH2:24][O:13][C:5]1[CH:6]=[C:7]([N+:10]([O-:12])=[O:11])[CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 94922,5-DinitrophenolHCID 11430Potassium CarbonateHCID 131802-Butene, 1,4-dibromo-

Product 1

HCID 739940351-Bromo-4-(2,5-dinitrophenyloxy)but-2-ene

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 2,5-dinitrophenol (4.0 g), potassium carbonate (4.6 g), NMP (40 mL) and 1,4-dibromo-2-butene (14.0 g) is heated to 45° C. for 2 hr. Extraction in the normal fashion and Kugelrohr distillation of the excess dibromide (0.1 mm Hg, 80° C.) gives 1-bromo-4-(2,5-dinitrophenyloxy)but-2-ene (mp 81-83° C.).

Workup

  1. extractionExtraction
  2. distillationin the normal fashion and Kugelrohr distillation of the excess dibromide (0.1 mm Hg, 80° C.)

Sources & evidence

ORD record
ord-f5e80ea4bce44aebb9b6189df4f7579d
Source dataset
uspto-grants-2004_03
Patent number
US06713135B2

Linked notes

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