3-Bromo-2-chloro-6-methylpyridine → 3-Bromo-2-methoxy-6-methylpyridine

HRID 1518962

反応式

HRID 1518962 の反応式
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.[CH3:10][O-:11].[Na+]>O1CCCC1>[Br:1][C:2]1[C:3]([O:11][CH3:10])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 27344183-Bromo-2-chloro-6-methylpyridineHCID 10942334Sodium Methoxide2 回

生成物 1

HCID 219525873-Bromo-2-methoxy-6-methylpyridine収率 46.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a cooled (0° C.) solution of 3-bromo-2-chloro-6-methylpyridine (300 mg, 1.45 mmol) in tetrahydrofuran (20 mL), add sodium methoxide (1.57 g, 29 mmol), slowly with stirring. Allow the mixture to warm to ambient temperature and stir overnight. Add additional sodium methoxide (500 mg) and stir at 100° C. overnight. Quench with water (20 mL), extract three times with ethyl acetate (30 mL). Combine the organics and wash with water then brine, and dry over sodium sulphate. Filter and concentrate to give the title product as a yellow solid (135 mg, 46%). 1HNMR (MeOH-d4): δ 7.72 (d, 1H), 6.70 (d, 1H), 3.93 (s, 3H), 2.38 (s, 3H).

後処理

  1. stirringstir overnight
  2. stirringstir at 100° C. overnight
  3. customQuench with water (20 mL)
  4. extractionextract three times with ethyl acetate (30 mL)
  5. washCombine the organics and wash with water
  6. dry with materialbrine, and dry over sodium sulphate
  7. filtrationFilter
  8. concentrationconcentrate

出典と根拠

ORDレコード
ord-8d366de7535d4acfbe9c4cc74166b2f9
出典データセット
uspto-grants-2015_07
特許番号
US09073856B2

関連ノート

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