N-bromobutanimide → Ethyl 6-(bromomethyl)picolinate

HRID 1162583

반응식

HRID 1162583 반응식
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[N:7]=1)=[O:5])[CH3:2].C1C(=O)N([Br:20])C(=O)C1>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][Br:20])[N:7]=1)=[O:5])[CH3:2]

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 564597Ethyl 6-methylpyridine-2-carboxylate

생성물 1

HCID 23033755Ethyl 6-(bromomethyl)picolinate수율 98.3%

시약·촉매·용매 2

HCID 7187Benzoyl Peroxide촉매HCID 5943Carbon Tetrachloride용매

실험 절차

A mixture of 6-methyl-pyridine-2-carboxylic acid ethyl ester (1.65 g, 10 mmol), NBS (1.77 g, 10 mmol), and benzoyl peroxide (100 mg) in carbon tetrachloride (20 ml) was refluxed for 14 h. After cooling to room temperature, the reaction mixture was partitioned between diethyl ether and water (120 ml, 4:1), organic layer was washed with water (2×20 ml), brine, dried (MgSO4), filtered and concentrated to give 6-bromomethyl-pyridine-2-carboxylic acid ethyl ester (2.4 g) which was used without further purification. LCMS m/z: 245 (M+1)+.

후처리

  1. temperaturewas refluxed for 14 h
  2. customthe reaction mixture was partitioned between diethyl ether and water (120 ml, 4:1), organic layer
  3. washwas washed with water (2×20 ml), brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-68468710087740078ac5874558b61ab5
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07820704B2

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