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

HRID 1034105

反応式

HRID 1034105 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 152407024-Propyl-3'-fluoro-4'-cyanotolan収率 22.8%

試薬・触媒・溶媒 2

HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c326cee72a404174aca5c46ee04e2104
出典データセット
uspto-grants-1994_05
特許番号
US05314640

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