Hydrochloric Acid → 4-Propyl-3'-fluoro-4'-cyanotolan

HRID 1034105Notes

Reaction equation

HRID 1034105 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6](I)=[CH:5][C:4]=1[F:10])#[N:2].[CH2:11]([C:14]1[CH:19]=[CH:18][C:17]([C:20]#[CH:21])=[CH:16][CH:15]=1)[CH2:12][CH3:13].Cl>CN(C)C=O.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:11]([C:14]1[CH:15]=[CH:16][C:17]([C:20]#[C:21][C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[C:4]([F:10])[CH:5]=2)=[CH:18][CH:19]=1)[CH2:12][CH3:13]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 27745182-Fluoro-4-iodobenzonitrileHCID 27751331-Ethynyl-4-propylbenzene

Product 1

HCID 152407024-Propyl-3'-fluoro-4'-cyanotolanYield 22.8%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

2.1 g of this 1-cyano-2-fluoro-4-iodobenzene was dissolved in 14 ml of N,N-dimethylformamide to which was added 3 mg of bis(triphenylphosphine) palladium (II) chloride and 13 mg of cuprous iodide. Next, 1.2 g of the 4-propylphenylacetylene obtained in step 2 was added and allowed to react at 50 to 60° C for 0.5 hour. After completion of the reaction, 35 ml of 9% hydrochloric acid was added to the reaction solution. After being extracted with chloroform, the crystals were washed with water three times to distill off the chloroform. The residue was purified by silica gel-chloroform column chromatography, followed by recrystallization with a mixed solvent of acetone and methanol to obtain 0.5 g of 4-propyl-3'-fluoro-4'-cyanotolan. The melting point of this compound (hereinafter referred to as the C-I point) was 67.2° C.

Workup

  1. customto react at 50 to 60° C for 0.5 hour
  2. additionwas added to the reaction solution
  3. extractionAfter being extracted with chloroform
  4. washthe crystals were washed with water three times
  5. distillationto distill off the chloroform
  6. customThe residue was purified by silica gel-chloroform column chromatography
  7. customfollowed by recrystallization with a mixed solvent of acetone and methanol

Sources & evidence

ORD record
ord-c326cee72a404174aca5c46ee04e2104
Source dataset
uspto-grants-1994_05
Patent number
US05314640

Reaction notes

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