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Nitric Acid → Propane, 1,2-dichloro-2-fluoro-3-nitro-

HRID 893406
Notes
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Reaction equation

HRID 893406 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Cl:5][C:6]([CH2:8][Cl:9])=[CH2:7].[FH:10]>>[Cl:5][C:6]([F:10])([CH2:8][Cl:9])[CH2:7][N+:1]([O-:4])=[O:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 65652,3-DichloropropeneHCID 14917Hydrofluoric Acid

Product 1

HCID 10954045Propane, 1,2-dichloro-2-fluoro-3-nitro-

Procedure

To a mixture of 86 ml of anhydrous, 100% strength nitric acid and 300 ml of anhydrous hydrofluoric acid were added dropwise at -10° C. in the course of 3 hours 111 g (1 mol) of 2,3-dichloropropene. The reaction was slightly exothermic. After the dropwise addition had ceased, stirring was continued for a further 1 hour at -10° C. Then the mixture was poured on to ice and extracted using dichloromethane. The organic phase was washed with sodium hydrogencarbonate solution, dried over sodium sulphate and concentrated using a rotary evaporator. The crude product was distilled under an oil pump vacuum. This gave 115.8 g (=63% of theory) of product having a boiling point of 48° to 50° C. at 0.07 mbar and a Refractive Index nD20 of 1.4578 (at 24° C.). The product was 95.7% pure.

Workup

  1. additionAfter the dropwise addition
  2. additionThen the mixture was poured on to ice
  3. extractionextracted
  4. washThe organic phase was washed with sodium hydrogencarbonate solution
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. customa rotary evaporator
  8. distillationThe crude product was distilled under an oil pump vacuum
  9. customof 1.4578 (at 24° C.)

Sources & evidence

ORD record
ord-afec642ef1af4c7c96b1e22144e82fe1
Source dataset
uspto-grants-1992_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05124476

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes