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

HRID 1518962

반응식

HRID 1518962 반응식
[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

참가 물질

4

반응물 2

HCID 27344183-Bromo-2-chloro-6-methylpyridineHCID 10942334Sodium Methoxide2회

생성물 1

HCID 219525873-Bromo-2-methoxy-6-methylpyridine수율 46.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8d366de7535d4acfbe9c4cc74166b2f9
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073856B2

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