N-bromobutanimide → Methyl 6-(bromomethyl)pyridine-2-carboxylate

HRID 899500

반응식

HRID 899500 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[N:6]=1)=[O:4].C1C(=O)N([Br:19])C(=O)C1>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][Br:19])[N:6]=1)=[O:4]

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 73022Methyl 6-methylpyridine-2-carboxylate

생성물 1

HCID 21471714Methyl 6-(bromomethyl)pyridine-2-carboxylate수율 20.2%

시약·촉매·용매 2

HCID 7187Benzoyl Peroxide촉매HCID 5943Carbon Tetrachloride용매

실험 절차

6-Bromomethyl-pyridine-2-carboxylic acid methyl ester was prepared according to Wells, G. J. et al. (WO 94/11398): A mixture of 6-methyl-pyridine-2-carboxylic acid methyl ester (6.5 g, 43.0 mmol), benzoyl peroxide (25 mg, 0.1 mmol) and NBS (8.5 g, 47.8 mmol) in carbon tetrachloride (250 mL) was heated at reflux overnight. The reaction mixture was cooled to room temperature, filtered, evaporated, and purified by chromatography on flash silica gel, eluting with 15% ethyl acetate/hexane to give 6-bromomethyl-pyridine-2-carboxylic acid methyl ester (2.0 g, 20%) as a white solid. 1HNMR (CDCl3): 6 8.06 (d, J=8.0 Hz, 1H), 7.87 (dd, J=8.0 Hz, 1H), 7.70 (d, J=8.0 Hz, 1H), 4.65 (s, 2H MS (APCI+): 231 (45), 235 (42).

후처리

  1. custom6-Bromomethyl-pyridine-2-carboxylic acid methyl ester was prepared
  2. temperaturewas heated
  3. temperatureat reflux overnight
  4. filtrationfiltered
  5. customevaporated
  6. custompurified by chromatography on flash silica gel
  7. washeluting with 15% ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-1d7b259dd06740e08cb6f08f6644e98a
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07355049B2

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