Sulfuric Acid → 2-Methyl-3,4,6-trifluorobenzonitrile

HRID 1272

反応式

HRID 1272 の反応式
[CH3:1][C:2]1[C:8]([F:9])=[C:7]([F:10])[CH:6]=[C:5]([F:11])[C:3]=1N.S(=O)(=O)(O)O.N([O-])=O.[Na+].[C-:21]#[N:22].[K+].[OH-].[NH4+]>S([O-])([O-])(=O)=O.[Cu+2].O>[CH3:1][C:2]1[C:8]([F:9])=[C:7]([F:10])[CH:6]=[C:5]([F:11])[C:3]=1[C:21]#[N:22]

参加物

8

反応物 5

HCID 1118Sulfuric AcidHCID 9032Potassium CyanideHCID 14923Ammonium HydroxideHCID 226251783,4,6-Trifluoro-2-methylanilineHCID 23668193Sodium Nitrite

生成物 1

HCID 226251752-Methyl-3,4,6-trifluorobenzonitrile収率 38.2%

試薬・触媒・溶媒 2

HCID 24462Copper Sulfate触媒HCID 962Water溶媒2 回

実験手順

To 2-methyl-3,4,6-trifluoroaniline (10.6 g) is added a mixture of conc. sulfuric acid (13.8 ml) and water (46 ml) and the mixture is cooled. Thereto an aqueous solution (20 ml) of sodium nitrite (5.5 g) is added dropwise at 0°-5° C. The solution is gradually added to a mixture of copper (II) sulfate 5 hydrate (41 g), potassium cyanide (43 g), ammonium hydroxide (60 ml) and water (260 ml) at 10°-30° C. The mixture is extracted with dichloromethane and the extract is dried over sodium sulfate, concentrated and the residue is purified with column chromatography (silica-gel, dichloromethane:n-hexane=1:4) to give 2-methyl-3,4,6-trifluorobenzonitrile (4.3 g).

後処理

  1. temperaturethe mixture is cooled
  2. extractionThe mixture is extracted with dichloromethane
  3. dry with materialthe extract is dried over sodium sulfate
  4. concentrationconcentrated
  5. customthe residue is purified with column chromatography (silica-gel, dichloromethane:n-hexane=1:4)

出典と根拠

ORDレコード
ord-1e9ca78c8b7943d3b81ed784f0fbf2a2
出典データセット
uspto-grants-1998_03
特許番号
US05723648

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