Nitric Acid → 1,2-Dichloro-1,2-difluoro-1-nitroethyl trifluoroacetate

HRID 2253553Notes

Reaction equation

HRID 2253553 reaction equation
ClC(F)([N+]([O-])=O)C(O)=O.OS(O)(=O)=O.O=S(=O)=O.[F:19][C:20]([F:25])([F:24])[C:21]([OH:23])=[O:22].[N+:26]([O-:29])(O)=[O:27].FC(F)(F)C(O)=O.[Cl:37][C:38]([F:42])=[C:39]([F:41])[Cl:40]>OS(O)(=O)=O.O=S(=O)=O>[F:19][C:20]([F:25])([F:24])[C:21]([O:23][C:38]([Cl:37])([F:42])[C:39]([Cl:40])([F:41])[N+:26]([O-:29])=[O:27])=[O:22]

Participants

7

Reactant 5

HCID 944Nitric AcidHCID 6422Trifluoroacetic acidHCID 11736DichlorodifluoroetheneHCID 13452256Chlorofluoronitroacetic AcidHCID 131718034Oleum Trifluoroacetic Acid

Product 1

HCID 538811491,2-Dichloro-1,2-difluoro-1-nitroethyl trifluoroacetateYield 14.5%

Reagents, catalysts & solvents 1

HCID 24681Fuming sulfuric acidSolvent

Procedure

Chlorofluoronitroacetic Acid, Oleum-Trifluoroacetic Acid Procedure. A solution of 100% nitric acid (5 mL) and trifluoroacetic acid (4.2 mL, 54 mmol) in 30% oleum (6 mL) was added over 25 min to 1,2-dichlorodifluoroethylene (7.5 g, 56 mmol) at 10°-15° C. The mixture was stirred for 60 min at 10°-14° C. The organic layer was separated, and fractionally distilled to give 2.1 g (14.5%) of 1,2-dichloro-1,2-difluoro-1-nitroethyl trifluoroacetate, as a 50:50 mixture of diasterimers, bp 48°-50° C. (0.5 mm): 19F NMR (CDCl3 ) δ -76.27 (s, 6 F), -77.50 (s,1 F), -78.49 (s, 1F), -94.37 (s, 1 F), -95.30 (s, 1 F). The second fraction contained 4.0 g of chlorofluoronitroacetic acid, bp 55°-65° C. (0.5 mm), identical to the authentic material prepared above. The oleum layer was heated to 80° C. under vacuum (0.5 mm) to give an additional 1.61 g (63% combined yield) of chlorofluoronitroacetic acid.

Workup

  1. customThe organic layer was separated
  2. distillationfractionally distilled

Sources & evidence

ORD record
ord-ebbc716f35704f0699fb2853a54618dd
Source dataset
uspto-grants-1993_08
Patent number
USH0001223

Reaction notes

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