Acetic Acid → 5-Bromo-2-fluoropyridin-3-ol

HRID 1685411ノート

反応式

HRID 1685411 の反応式
[Br:1][C:2]1[CH:3]=[C:4](B(O)O)[C:5]([F:8])=[N:6][CH:7]=1.C(O)(=[O:14])C.C(OCC)(=O)C.OO>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([OH:14])[C:5]([F:8])=[N:6][CH:7]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 8857Ethyl AcetateHCID 27832425-Bromo-2-fluoropyridine-3-boronic Acid (contains varying amounts of Anhydride)

生成物 1

HCID 201118655-Bromo-2-fluoropyridin-3-ol収率 62%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
35 °C

実験手順

A solution of 1.36 g (6.18 mM) of 5-bromo-2-fluoro-3-pyridineboronic acid in a mixture of 9.5 ml of ethanol, 2.3 ml of acetic acid and 1.3 ml of ethyl acetate is prepared. 2.2 ml of 30% hydrogen peroxide are added to the solution. The reaction mixture is stirred at a temperature of 35° C. for 3 hours and then cooled and extracted with ethyl ether. The organic phases are washed with a solution of ferrous ammonium sulfate, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The solid residue is purified by chromatography on silica gel using a toluene/ethyl acetate mixture (9/1; v/v) as the eluent to give the desired product in the form of a white solid with a yield of 62%.

後処理

  1. customis prepared
  2. temperaturecooled
  3. extractionextracted with ethyl ether
  4. washThe organic phases are washed with a solution of ferrous ammonium sulfate
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe solid residue is purified by chromatography on silica gel using a toluene/ethyl acetate mixture (9/1; v/v) as the eluent

出典と根拠

ORDレコード
ord-240c76788df04d8cb985f26908ccdd5a
出典データセット
uspto-grants-2012_04
特許番号
US08148407B2

反応ノート

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