Ethanol → Vinylpentafluorocyclopropane

HRID 2260769Notes

Reaction equation

HRID 2260769 reaction equation
[OH-].[K+].C(O)C.Br[CH2:7][CH2:8][C:9]1([F:16])[C:11]([F:13])([F:12])[C:10]1([F:15])[F:14]>O>[CH:8]([C:9]1([F:16])[C:11]([F:13])([F:12])[C:10]1([F:15])[F:14])=[CH2:7]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 18999018(2-Bromoethyl)(pentafluoro)cyclopropane

Product 1

HCID 11446484VinylpentafluorocyclopropaneYield 57.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 18.0 g of KOH, 15 mL of ethanol and 20 mL of water was slowly added 24.0 g of 2-bromo-1-(pentafluorocyclopropyl)ethane at 70° C. During the addition, volatiles were collected in a -78° C. trap. After the addition was complete, the reaction mixture was stirred at 70° C. for an additional two hours until collection of all volatiles, which was distilled to give 9.1 g of product, bp 30° C. 19F NMR: -152.3 (dt, J =195.4 Hz, J=9.8 Hz, 2F), -156.0 (dm, J=195.6 Hz, 2F), -210.7 (t, J=7.7 Hz, 1F) . 1H NMR: 5.86-5.73 (m, 2H), 5.70-5.65 (m, 1H).

Workup

  1. customat 70° C
  2. additionDuring the addition, volatiles
  3. customwere collected in a -78° C. trap
  4. additionAfter the addition
  5. distillationwas distilled

Sources & evidence

ORD record
ord-e2cd9ca87ee7481084adbce35ae0f015
Source dataset
uspto-grants-1995_12
Patent number
US05478904

Reaction notes

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