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

HRID 1054103

반응식

HRID 1054103 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

HCID 159459965-(Bromomethyl)-2-phenylpyridine

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

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]+.

후처리

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

출처 및 근거

ORD 기록
ord-6014722e39444eeab6e7833b2bcbe9b1
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394290B2

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