Hydrochloric Acid → 4-Propyl-3',5'-difluoro-4'-cyanotolan

HRID 1034109

反応式

HRID 1034109 の反応式
[F:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[C:4]([F:9])[C:3]=1[C:10]#[N:11].[CH2:12]([C:15]1[CH:20]=[CH:19][C:18]([C:21]#[CH:22])=[CH:17][CH:16]=1)[CH2:13][CH3:14].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>[CH2:12]([C:15]1[CH:16]=[CH:17][C:18]([C:21]#[C:22][C:6]2[CH:7]=[C:2]([F:1])[C:3]([C:10]#[N:11])=[C:4]([F:9])[CH:5]=2)=[CH:19][CH:20]=1)[CH2:13][CH3:14]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 27751331-Ethynyl-4-propylbenzeneHCID 190230682,6-Difluoro-4-iodobenzonitrile

生成物 1

HCID 678200934-Propyl-3',5'-difluoro-4'-cyanotolan収率 27.3%

試薬・触媒・溶媒 2

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

実験手順

5.6 g of this 1,3-difluoro-2-cyano-5-iodobenzene was dissolved in 35 ml of N,N-dimethylformamide, to which was added 7.3 mg of bis(triphenylphosphine) palladium (II) chloride and 34 m of cuprous iodide. Next, 3 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 1.6 g of 4-propyl-3',5'-difluoro-4'-cyanotolan. The melting (C-I) point of this compound was 83.3° 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-96dca59ae695483485b56915baabee13
出典データセット
uspto-grants-1994_05
特許番号
US05314640

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