5-Methyl-2-phenylpyridine → 5-(Bromomethyl)-2-phenylpyridine

HRID 1054103

反応式

HRID 1054103 の反応式
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:6][CH:7]=1.C1C(=O)N([Br:21])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:21][CH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[N:6][CH:7]=1

参加物

4

反応物 2

HCID 474675-Methyl-2-phenylpyridineHCID 67184N-bromobutanimide

生成物 1

HCID 159459965-(Bromomethyl)-2-phenylpyridine

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

Synthesized using compound 61b (760 mg, 4.49 mmol), NBS (878 mg, 4.93 mmol) and DBPO (54 mg, 0.23 mmol) in carbon tetrachloride according to Method A. Crude product was purified by flash chromatography on silica-gel using hexane/ethyl acetate (8:1) as eluent. White solid. Yield: 297 mg, 73%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=4.54 (s, 2H), 7.42-7.53 (m, 3H), 7.71-7.77 (m, 1H), 7.80-7.85 (m, 1H), 7.98-8.04 (m, 2H), 8.72-8.76 (m, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=29.7, 120.6, 127.0, 128.4, 128.8, 130.1, 137.6, 138.5, 149.6, 157.36; (ESI): m/z=249.66 [M+H]+.

後処理

  1. customSynthesized
  2. customCrude product was purified by flash chromatography on silica-gel

出典と根拠

ORDレコード
ord-6014722e39444eeab6e7833b2bcbe9b1
出典データセット
uspto-grants-2016_07
特許番号
US09394290B2

関連ノート

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