Dichloromethane → 5-Bromo-2,3-dimethoxypyridine

HRID 1162451

반응식

HRID 1162451 반응식
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][N:4]=1.C(Cl)Cl.[Br:14]Br>C([O-])(O)=O.[Na+]>[Br:14][C:6]1[CH:7]=[C:8]([O:9][CH3:10])[C:3]([O:2][CH3:1])=[N:4][CH:5]=1

참가 물질

5

반응물 3

HCID 6344DichloromethaneHCID 24408BromineHCID 46578092,3-Dimethoxypyridine

생성물 1

HCID 125630845-Bromo-2,3-dimethoxypyridine수율 64.9%

시약·촉매·용매 1

HCID 516892Sodium Bicarbonate용매

실험 절차

To a 100 mL round-bottomed flask was added 2,3-dimethoxypyridine (2 mL, 15 mmol, Alfa Aesar, Ward Hill, Mass.), CH2Cl2 (30 mL), and bromine (0.7 mL, 14 mmol). The reaction mixture was stirred at rt for 16 h. The reaction mixture was then diluted with sat. NaHCO3 (30 mL) and extracted with EtOAc (2×50 mL). The combined organic extracts were washed with sat. NaCl (20 mL), dried over Na2SO4, filtered and concentrated. Purification by silica gel chromatography (50% CH2Cl2/hexanes) afforded the title compound (1.98 g, 60%). MS (ESI, positive ion) m/z: 218 (M(79Br)+1).

후처리

  1. extractionextracted with EtOAc (2×50 mL)
  2. washThe combined organic extracts were washed with sat. NaCl (20 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (50% CH2Cl2/hexanes)

출처 및 근거

ORD 기록
ord-08016a45d69e42e1b8eee1f95839037d
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07820665B2

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