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

HRID 72659ノート

反応式

HRID 72659 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-836af7366fa74fcda1241520e5f003c4
出典データセット
uspto-grants-2014_09
特許番号
US08829003B2

反応ノート

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