Potassium Hydroxide → 5-(Difluoromethoxy)-4-iodo-2-methoxypyridine

HRID 56855

反応式

HRID 56855 の反応式
[OH-].[K+].[I:3][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[N:7]=[CH:6][C:5]=1[OH:12].[F:13][C:14](F)([F:22])S(OC(F)F)(=O)=O>C(#N)C.O>[F:13][CH:14]([F:22])[O:12][C:5]1[C:4]([I:3])=[CH:9][C:8]([O:10][CH3:11])=[N:7][CH:6]=1

参加物

6

反応物 3

HCID 14797Potassium HydroxideHCID 542802Difluoromethyl trifluoromethanesulfonateHCID 120277864-Iodo-6-methoxypyridin-3-ol

生成物 1

HCID 1176053175-(Difluoromethoxy)-4-iodo-2-methoxypyridine

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

4.8 ml of aqueous potassium hydroxide solution (6M) were added to a solution of 600 mg (purity 93%, 2.22 mmol) of 4-iodo-6-methoxypyridin-3-ol in 4.8 ml of acetonitrile, the mixture was cooled in an ice bath and 863 μl (purity 75%, 3.56 mmol, 1.6 eq.) of difluoromethyl trifluoromethanesulphonate [Angew. Chem. Int. Ed. 2013, 52, 1-5; Journal of Fluorine Chemistry 2009, 130, 667-670] were added with vigorous stirring. The reaction mixture was stirred for 2 min and diluted with 33 ml of water. The aqueous phase was extracted twice with in each case 40 ml of diethyl ether. The combined organic phases were dried (sodium sulphate), filtered, concentrated under reduced pressure and dried. The crude product was purified by flash chromatography (IR-50SI, petroleum ether/ethyl acetate 12-20%). Yield: 407 mg (purity 90%, 55% of theory)

後処理

  1. temperaturethe mixture was cooled in an ice bath
  2. extractionThe aqueous phase was extracted twice with in each case 40 ml of diethyl ether
  3. dry with materialThe combined organic phases were dried (sodium sulphate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customdried
  7. customThe crude product was purified by flash chromatography (IR-50SI, petroleum ether/ethyl acetate 12-20%)

出典と根拠

ORDレコード
ord-fcb6b0de660543c1a3e2b855c42f019b
出典データセット
uspto-grants-2016_09
特許番号
US09434690B2

関連ノート

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