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

HRID 1054103Notes

Reaction equation

HRID 1054103 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 159459965-(Bromomethyl)-2-phenylpyridine

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

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]+.

Workup

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

Sources & evidence

ORD record
ord-6014722e39444eeab6e7833b2bcbe9b1
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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