Sulfuric Acid → 3-Bromo-4-chloro-2,6-dimethylpyridine

HRID 1043917ノート

反応式

HRID 1043917 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([CH3:9])[CH:3]=1.FC(F)(F)C(O)=O.S(=O)(=O)(O)O.C1C(=O)N([Br:29])C(=O)C1.[OH-].[Na+]>>[Br:29][C:3]1[C:4]([CH3:9])=[N:5][C:6]([CH3:8])=[CH:7][C:2]=1[Cl:1]

参加物

6

反応物 5

HCID 1118Sulfuric AcidHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 5881754-Chloro-2,6-dimethylpyridine

生成物 1

HCID 129999523-Bromo-4-chloro-2,6-dimethylpyridine収率 21.4%

実験手順

4-chloro-2,6-dimethylpyridine (1.5 g) was added to a mixed solvent of trifluoroacetic acid (3 mL) and concentrated sulfuric acid (6 mL). NBS (22 g) was added to the solution, and the mixture was stirred at room temperature for 12 hours. A 5 N aqueous sodium hydroxide solution was added to the reaction mixture, followed by separation with ethyl acetate. The organic layer was washed with brine and then dried over anhydrous magnesium sulfate. The desiccant was removed by filtration, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 5% to 30%) to give the title compound (500 mg).

後処理

  1. customfollowed by separation with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe desiccant was removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 5% to 30%)

出典と根拠

ORDレコード
ord-e41be24f0a274bd5b52c552b0224499c
出典データセット
uspto-grants-2013_10
特許番号
US08563565B2

反応ノート

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