Ethanol → HCID 13055446, compound

HRID 1703356Notes

Reaction equation

HRID 1703356 reaction equation
I[CH:2]([CH2:8][C:9]([F:15])([F:14])[C:10]([F:13])([F:12])[Br:11])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[N-:16]=[N+:17]=[N-:18].[Na+].C(O)C.N(C(CC(F)(F)C(F)(F)Br)C([O-])=O)=[N+]=[N-]>O>[N:16]([CH:2]([CH2:8][C:9]([F:15])([F:14])[C:10]([F:13])([F:12])[Br:11])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[N+:17]=[N-:18]

Participants

6

Reactant 4

HCID 702EthanolHCID 33557Sodium AzideHCID 13055445HCID 13055445, compoundHCID 20523989HCID 20523989, compound

Product 1

HCID 13055446HCID 13055446, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Subsequently, 9.7 g (0.024 mol) of ethyl 2-iodo-4,4,5,5-tetrafluoro-5-bromopentanoate and 2.73 g (0.042 mol) of sodium azide were added to 40 ml of 80% ethanol and were refluxed while under stirring at an elevated temperature for one hour. Then water was added to the resultant mixture and 2-azido-4,4,5,5-tetrafluoro-5-bromopentanoate was extracted with ether, whereafter the ether was removed by drying. The residual liquid was vacuum distilled to afford 4.54 g (0.014 mol, yield of 60%) of ethyl 2-azido-4,4,5,5-tetrafluoro-5-bromopentanoate having b.p. 78° to 79° C./4 mm, nD20 1.4291, d420 1.564, νN3 2120 cm-1 and νC=O 1746 cm-1.

Workup

  1. temperaturewere refluxed while
  2. extractionwas extracted with ether, whereafter the ether
  3. customwas removed
  4. customby drying
  5. distillationdistilled

Sources & evidence

ORD record
ord-7d72a65655d445ef92a6648dea8cd110
Source dataset
uspto-grants-1982_09
Patent number
US04351954

Reaction notes

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