Benzoyl Peroxide → 3-Methoxy-2-nitro-6-pyridylmethyl bromide

HRID 72659

반응식

HRID 72659 반응식
[CH3:1][O:2][C:3]1[C:4]([N+:10]([O-:12])=[O:11])=[N:5][C:6]([CH3:9])=[CH:7][CH:8]=1.C1C(=O)N([Br:20])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[OH-].[Na+]>C(Cl)(Cl)(Cl)Cl>[Br:20][CH2:9][C:6]1[N:5]=[C:4]([N+:10]([O-:12])=[O:11])[C:3]([O:2][CH3:1])=[CH:8][CH:7]=1

참가 물질

6

반응물 4

HCID 7187Benzoyl PeroxideHCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 27279653-Methoxy-6-methyl-2-nitropyridine

생성물 1

HCID 144051243-Methoxy-2-nitro-6-pyridylmethyl bromide

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

A mixture of 3-methoxy-6-methyl-2-nitropyridine (10.08 g, 60 mmol), NBS (9.79 g, 55 mmol), and benzoyl peroxide (2 g, 6 mmol) in CCl4 (250 mL) was refluxed for 56 hours under nitrogen atmosphere. The reaction mixture was added 100 mL 1M NaOH aq. and extracted using ethyl acetate (3×300 mL). The combined organic layer was dried over Mg2SO4 and filtered. The solvent was evaporated to yield a brown oily. 1H-NMR (CDCl3): δ 3.99 (s, 3H, OCH3), 4.51 (s, 2H, CH2), 7.55 (d, 1H, J=8.8 Hz, Py-H), 7.70 (d, 1H, J=8.4 Hz, Py-H). HR-MS (ESI+) m/z 246.9600 [M+1]+ C7H7BrN2O3 requires 245.9640.

후처리

  1. temperaturewas refluxed for 56 hours under nitrogen atmosphere
  2. extractionextracted
  3. dry with materialThe combined organic layer was dried over Mg2SO4
  4. filtrationfiltered
  5. customThe solvent was evaporated
  6. customto yield a brown oily

출처 및 근거

ORD 기록
ord-836af7366fa74fcda1241520e5f003c4
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829003B2

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