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

HRID 394167노트

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HRID 394167 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

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온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8c9e8154d86c4d20b1a5188c8134d260
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06809199B2

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