N-bromobutanimide → 5-Bromo-1-(bromomethyl)-2-fluoro-3-methylbenzene

HRID 1880431

반응식

HRID 1880431 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH3:10])[C:5]([F:9])=[C:6]([CH3:8])[CH:7]=1.[Br:11]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([F:9])=[C:4]([CH2:10][Br:11])[CH:3]=1

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 27362985-Bromo-2-fluoro-1,3-dimethylbenzene

생성물 1

HCID 669206545-Bromo-1-(bromomethyl)-2-fluoro-3-methylbenzene수율 100.7%

시약·촉매·용매 2

HCID 7187Benzoyl Peroxide촉매HCID 5943Carbon Tetrachloride용매

실험 절차

To a stirred solution of 5-bromo-2-fluoro-1,3-dimethylbenzene (5.0 g, 25 mmol) in carbon tetrachloride (100.0 mL) was added N-bromosuccinimide (4.11 g, 23.1 mmol) and benzoyl peroxide (100.0 mg, 0.017 mmol). The reaction was heated at reflux for 7 hours. The reaction was filtered and the filtrate washed with 2N HCl, saturated aqueous sodium bicarbonate, water and brine. The organic phase was dried over sodium sulfate, filtered and concentrated. The residue was flash chromatographed (5% EtoAc/Haptanes) to obtain 6.56 g of 5-bromo-1-(bromomethyl)-2-fluoro-3-methylbenzene as an oil product. 1H NMR (400 MHz, CDCl3) δ ppm 2.22-2.36 (s, 3 H) 4.42 (d, J=0.98 Hz, 2 H) 7.21-7.37 (m, 2 H)

후처리

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 7 hours
  3. filtrationThe reaction was filtered
  4. washthe filtrate washed with 2N HCl, saturated aqueous sodium bicarbonate, water and brine
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed (5% EtoAc/Haptanes)

출처 및 근거

ORD 기록
ord-4b345bc30f60488db40c42acdba3cf03
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318762B2

연결된 노트

불러오는 중…