Methanesulfonic Acid → 2-Chloro-3-(2,2,2-trifluoroethoxy)pyridine

HRID 50125

反応式

HRID 50125 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].CS(O)(=O)=O.S([O-])([O-])(=O)=O.[Mg+2].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

7

反応物 6

HCID 6395Methanesulfonic AcidHCID 64092,2,2-Trifluoroethanol2 回HCID 10906Tert-Butyl nitriteHCID 24083Sulfuric acid magnesium salt (1:1)HCID 805282-Chloro-3-pyridylamineHCID 516892Sodium Bicarbonate

生成物 1

HCID 120567282-Chloro-3-(2,2,2-trifluoroethoxy)pyridine収率 70.1%

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), methanesulfonic acid (2.02 g, 21 mmol), and magnesium sulfate (3 g). 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 65° C. to 70° C. After cooling the solution it is 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 (4.4 g) with an actual yield of 70.1%.

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. temperaturemaintained at 65° C. to 70° C
  4. temperatureAfter cooling the solution it
  5. extractionextracted with MTBE
  6. customThe solvent is removed by evaporation

出典と根拠

ORDレコード
ord-13c858555cab4c44b1e2deac7e473876
出典データセット
uspto-grants-2004_03
特許番号
US06710180B2

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