Benzoyl Peroxide → 4,6-Dibromo-3-(bromomethyl)-2-(2,4-difluorophenyl)pyridine

HRID 394167ノート

反応式

HRID 394167 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([Br:8])[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[F:16])[C:3]=1[CH3:17].[Br:18]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([Br:8])[N:5]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[F:16])[C:3]=1[CH2:17][Br:18]

参加物

5

反応物 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 226480394,6-Dibromo-2-(2,4-difluorophenyl)-3-methylpyridine

生成物 1

HCID 226481174,6-Dibromo-3-(bromomethyl)-2-(2,4-difluorophenyl)pyridine

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of 4,6-dibromo-2-(2,4-difluorophenyl)-3-methylpyridine (5.0 g, 13.77 mmol, 1 eq) in CCl4 (125 mL) was added N-bromosuccinimide (2.95 g, 16.6 mmol 1.2 eq) and benzoyl peroxide (340 mg, 1.37 mmol, 0.1 eq). The mixture was brought to and maintained at reflux until all the starting material was consumed (approx 3.5 h). The reaction mixture was cooled to 0° C. and the succinimide was filtered off. The solvent was removed under reduced pressure and the product was purified by flash column chromatography on silica gel elufing with 2% Et2O in hexanes giving 4,6-dibromo-3-(bromomethyl)-2-(2,4-difluorophenyl)pyridine. Mass spectrum (ESI) 440.1 (M+1); 442.1 (M+3); 444.1 (M+5); 446.1 (M+7). 1H NMR (500 MHz, CDCl3) δCHCl3: 7.84 (1H, s); 7.50 (1H, m); 7.05 (1H, m); 6.96 (1H, m); 4.44 (2H br s).

後処理

  1. temperaturemaintained
  2. temperatureat reflux until all the starting material
  3. customwas consumed (approx 3.5 h)
  4. filtrationthe succinimide was filtered off
  5. customThe solvent was removed under reduced pressure
  6. customthe product was purified by flash column chromatography on silica gel elufing with 2% Et2O in hexanes

出典と根拠

ORDレコード
ord-8c9e8154d86c4d20b1a5188c8134d260
出典データセット
uspto-grants-2004_10
特許番号
US06809199B2

反応ノート

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