Sodium Azide → 5-(2-Chloro-4-trifluoromethylphenoxy)-2-nitrophenyl azide

HRID 463597

Reaction equation

HRID 463597 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[C:7]([N+:14]([O-])=O)[CH:6]=1.[N-:25]=[N+:26]=[N-].[Na+]>CC(C)=O>[Cl:1][C:2]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[C:7]([N:14]=[N+:25]=[N-:26])[CH:6]=1

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 156238Benzene, 2-chloro-1-(3,4-dinitrophenoxy)-4-(trifluoromethyl)-

Product 1

HCID 135053575-(2-Chloro-4-trifluoromethylphenoxy)-2-nitrophenyl azide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-(2-chloro-4-trifluoromethylphenoxy)-1,2-dinitrobenzene (2.0 g, 5.5 mmol) and sodium azide (1.1 g, 16.6 mmol) in acetone (25 ml) is heated under reflux for 3.5 hours. The reaction is then cooled and filtered, and the filtrate is stripped. The residue is taken up in chloroform, washed with water (2X) and with brine, dried, stripped and purified by preparative thin layer chromatography (prep. TLC) (silica gel, eluting with 15% ethyl acetate/hexane) to give 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrophenyl azide.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 3.5 hours
  3. temperatureThe reaction is then cooled
  4. filtrationfiltered
  5. washwashed with water (2X) and with brine
  6. customdried
  7. custompurified by preparative thin layer chromatography (prep. TLC) (silica gel, eluting with 15% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-6be467e2eaa24931ab7484da4a7a0218
Source dataset
uspto-grants-1985_10
Patent number
US04544400

Linked notes

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