HCID 21527506, compound → HCID 21527492, compound

HRID 1658477Notes

Reaction equation

HRID 1658477 reaction equation
Cl[C:2]([N:11]=[C:12]=[O:13])([C:7]([F:10])([F:9])[F:8])[C:3](Cl)([F:5])[F:4]>COCCOC.[Zn]>[F:4][C:3]([F:5])=[C:2]([N:11]=[C:12]=[O:13])[C:7]([F:9])([F:8])[F:10]

Participants

4

Reactant 1

HCID 21527506HCID 21527506, compound

Product 1

HCID 21527492HCID 21527492, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A 244 g sample (1.0 mole) of 1,2-dichloro-2,2-difluoro-1-(trifluoromethyl)ethyl isocyanate was added dropwise to a stirred suspension of 98 g (1.5 gram atom) of powdered zinc in 1000 ml of glycol dimethyl ether at such a rate that the temperature warmed to 45° and remained between 45°-50°. The reaction mixture was stirred for 1 hr after the addition, and then the most volatile portion was distilled under reduced pressure (5 mm) into a trap cooled oled to -78 °. The condensate in the trap was redistilled to give 158 g (91%) of 2,2-difluoro-1-(trifluoromethyl)vinyl isocyanate as a colorless liquid: bp 42.3-42.5°, ir (liquid), 4.38 μ (NCO) and 5.67 μ (=CF2); 19F nmr (CCl3F) δ 66.6 ppm (d, J = 9 Hz to d, J = 23 Hz, 3F) δ 82.9 ppm (d, J = 21 Hz to q, J = 9 Hz, IF) and δ 89.7 ppm (d, J = 21 Hz to d, J = 23 Hz, IF).

Workup

  1. temperaturewarmed to 45°
  2. customremained between 45°-50°
  3. additionafter the addition
  4. distillationthe most volatile portion was distilled under reduced pressure (5 mm) into a trap
  5. temperaturecooled
  6. customoled to -78 °
  7. distillationThe condensate in the trap was redistilled

Sources & evidence

ORD record
ord-1b5fa621369f4a3c9c94a40c6b8c173b
Source dataset
uspto-grants-1976_06
Patent number
US03965074

Reaction notes

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