Phosphorus oxide (P4O10) → Propanenitrile, 2,3,3,3-tetrafluoro-2-iodo-

HRID 1276571Notes

Reaction equation

HRID 1276571 reaction equation
[I:1][C:2]([F:10])([C:6]([F:9])([F:8])[F:7])[C:3]([NH2:5])=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>>[I:1][C:2]([F:10])([C:6]([F:9])([F:8])[F:7])[C:3]#[N:5]

Participants

3

Reactant 2

HCID 14812Phosphorus oxide (P4O10)HCID 135929822-Iodotetrafluoropropionamide

Product 1

HCID 12119968Propanenitrile, 2,3,3,3-tetrafluoro-2-iodo-

Conditions

Temperature
97.5 °C

Procedure

2-Iodotetrafluoropropionamide prepared from Experiment 6 (16.3 g, 0.06 mol) was mixed well with P2O5 (16.3 g, 0.115 mol) in a flask under nitrogen atmosphere. The mixture was heated slowly to 95 to 100° C., a volatile product started to form and was collected in a cold trap (dry ice-acetone bath). The title product was obtained as a slightly pink liquid after purification by distillation, yield 12.5 g (82.5%), b.p. 68-70° C. 19F NMR (188.24 MHz, CDCl3): -78.7 (2 singlets, 3F), -137.9 (q, J =16 Hz, 1F); IR: 2288 cm-1 (C≡N); Mass. Calcd. for [M+ ]: 252.9382; Found: 252.9012.

Workup

  1. customto form
  2. customwas collected in a cold trap (dry ice-acetone bath)

Sources & evidence

ORD record
ord-376e45dfc7724ea5ac2fb967eead9f67
Source dataset
uspto-grants-2000_12
Patent number
US06166157

Reaction notes

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