Benzoyl Peroxide → 4-Bromomethyl-2-fluoropyridine

HRID 82460

반응식

HRID 82460 반응식
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.[Br:9]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl.ClCCl>[Br:9][CH2:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([F:1])[CH:7]=1

참가 물질

6

반응물 3

HCID 7187Benzoyl Peroxide2회HCID 67184N-bromobutanimideHCID 27374032-Fluoro-4-methylpyridine

생성물 1

HCID 139851684-Bromomethyl-2-fluoropyridine

시약·촉매·용매 2

HCID 5943Carbon Tetrachloride용매HCID 6344Dichloromethane용매

반응 조건

온도
90 °C

실험 절차

To a solution of 2-fluoro-4-methylpyridine (0.510 g, 4.59 mmol) in 20 mL of carbon tetrachloride was added N-bromosuccinimide (0.899 g, 5.05 mmol) and benzoyl peroxide (0.148 g, 0.459 mmol). The mixture was heated to 90° C. for 1 h, and then additional benzoyl peroxide (0.074 g, 0.23 mmol) was added. After 20 h, the reaction was diluted with dichloromethane, washed 3× with water, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified via silica gel chromatography, eluting with 0-10% ethyl acetate in hexanes to provide the 4-(bromomethyl)-2-fluoropyridine that gave proton NMR spectra consistent with theory and a mass ion (ES+) of 191.9 (81Br) for [M+H]+.

후처리

  1. washwashed 3× with water
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified via silica gel chromatography
  6. washeluting with 0-10% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-26fd88478f0a49bca53fd2c9665016b2
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846702B2

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