Benzoyl Peroxide → Methyl 5-(bromomethyl)pyridine-2-carboxylate

HRID 1777538

반응식

HRID 1777538 반응식
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1.[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:12][CH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1

참가 물질

5

반응물 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 268759Methyl 5-methylpicolinate

생성물 1

HCID 19699469Methyl 5-(bromomethyl)pyridine-2-carboxylate

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

To a mixture of methyl 5-methylpicolinate (1.25 g; 8.27 mmol) in carbon tetrachloride (45 mL) was added N-bromosuccinimide (1.78 g, 9.92 mmol) and benzoyl peroxide (0.205 g; 0.827 mmol). The mixture was refluxed for 18 hours and the resulting suspension was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (eluent 0 to 8% ethyl acetate in dichloromethane) to 0.450 g (24%) of methyl 5-(bromomethyl)picolinate as a beige solid.

후처리

  1. temperatureThe mixture was refluxed for 18 hours
  2. concentrationthe resulting suspension was concentrated under reduced pressure
  3. customThe residue was purified by flash chromatography on silica gel (eluent 0 to 8% ethyl acetate in dichloromethane) to 0.450 g (24%) of methyl 5-(bromomethyl)picolinate as a beige solid

출처 및 근거

ORD 기록
ord-39f8b697f6ad48588debfcbbfb163201
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09266832B2

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