2,2,2-Trifluoroethanol → 2-Chloro-3-(2,2,2-trifluoroethoxy)pyridine

HRID 50124ノート

反応式

HRID 50124 の反応式
N[C:2]1[C:3]([Cl:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[F:9][C:10]([F:14])([F:13])[CH2:11][OH:12].FC(F)(F)C(O)=O.N(OC(C)(C)C)=O.C(=O)(O)[O-].[Na+]>>[Cl:8][C:3]1[C:2]([O:12][CH2:11][C:10]([F:14])([F:13])[F:9])=[CH:7][CH:6]=[CH:5][N:4]=1

参加物

6

反応物 5

HCID 64092,2,2-Trifluoroethanol2 回HCID 6422Trifluoroacetic acidHCID 10906Tert-Butyl nitriteHCID 805282-Chloro-3-pyridylamineHCID 516892Sodium Bicarbonate

生成物 1

HCID 120567282-Chloro-3-(2,2,2-trifluoroethoxy)pyridine収率 62.6%

反応条件

温度
55 °C

実験手順

A reactor vessel is charged with 3-amino-2-chloropyridine (2.7 g, 21 mmol), 2,2,2-trifluoroethanol (15 g, 150 mmol), and trifluoroacetic acid (3.63 g, 31.8 mmol). The solution is cooled to the range 0° C. to 5° C. and then the reagent t-butyl nitrite (2.51 g of a 96% solution, 23.4 mmol) is added drop-wise to the vessel maintaining the temperature in the range 0° C. to 5° C. After stirring a few minutes the solution is transferred drop-wise to a reactor vessel containing 2,2,2-trifluoroethanol (20 g, 200 mmol) maintained at 55° C. The temperature rose to 70° C. during the drop-wise addition of the diazonium salt reaction mass. After cooling the solution, it neutralized with aqueous saturated sodium bicarbonate solution and then extracted with MTBE. The solvent is removed by evaporation to obtain 2-chloro-3-(2,2,2-trifluoroethoxy)pyridine as a crude oil (3.36 g) with an actual yield of 62.6%.

後処理

  1. temperatureThe solution is cooled to the range 0° C. to 5° C.
  2. temperaturemaintaining the temperature in the range 0° C. to 5° C
  3. temperatureAfter cooling the solution, it
  4. extractionextracted with MTBE
  5. customThe solvent is removed by evaporation

出典と根拠

ORDレコード
ord-6692566b87734cbdb07afed6ba1ac6e2
出典データセット
uspto-grants-2004_03
特許番号
US06710180B2

反応ノート

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