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

HRID 50519

Reaction equation

[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[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]=[CH:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

Conditions

Temperature: 45 °C

Procedure

A mixture of 2,4-dinitrophenol (4.6 g, 80 wt %), potassium carbonate (4.2 g), NMP (40 mL) and 1,4-dibromo-2-butene (12.8 g) was 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.) gave 1-bromo-4-(2,4-dinitrophenyloxy)but-2-ene (3.7 g, mp 55-57° C.).

Workup

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

Sources & evidence

ORD record: ord-001383a7dc4048e8b945bdebc5387987
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06713135B2

Linked notes

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