Potassium Carbonate → 4-[1-(Trifluoromethyl)ethenyl]pyridine

HRID 1880770

Reaction equation

HRID 1880770 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[F:14][C:15]([F:22])([F:21])[C:16](B(O)O)=[CH2:17].[Cl-].[NH4+]>O1CCOCC1>[F:14][C:15]([F:22])([F:21])[C:16]([C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1)=[CH2:17]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 6094924-IodopyridineHCID 2782677(3,3,3-Trifluoroprop-1-en-2-yl)boronic acid

Product 1

HCID 595703554-[1-(Trifluoromethyl)ethenyl]pyridineYield 73.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To 1,4-dioxane were added 3.22 g of 4-iodopyridine, 10.87 g of potassium carbonate, 0.036 g of tetrakis(triphenylphosphinepalladium) and 5.5 g of 1-(trifluoromethyl)vinylboronic acid, and the mixture was stirred at 110° C. for 8 hours. Thereafter, this solution was poured into an aqueous saturated ammonium chloride solution, followed by extraction with diethyl ether three times. The organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 2.0 g of 4-[1-(trifluoromethyl)ethenyl]pyridine.

Workup

  1. extractionfollowed by extraction with diethyl ether three times
  2. washwashed with an aqueous saturated sodium chloride solution
  3. dry with materialdried with anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9f0c2151f2b44a58a621a8a51def4c6e
Source dataset
uspto-grants-2012_11
Patent number
US08318776B2

Linked notes

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