N-bromobutanimide → 2-(Bromomethyl)-1-chloro-4-iodobenzene

HRID 1169874노트

반응식

HRID 1169874 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][C:3]=1[CH3:9].[Br:10]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:10][CH2:9][C:3]1[CH:4]=[C:5]([I:8])[CH:6]=[CH:7][C:2]=1[Cl:1]

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 42009962-Chloro-5-iodotoluene

생성물 1

HCID 117390382-(Bromomethyl)-1-chloro-4-iodobenzene수율 55%

시약·촉매·용매 2

HCID 7187Benzoyl Peroxide촉매HCID 5943Carbon Tetrachloride용매

실험 절차

A mixture of 2-chloro-5-iodo-toluene (0.5 g, 1.98 mmol), N-bromosuccinimide (0.422 g, 2.35 mmol) and benzoyl peroxide (21.5 mg, 0.089 mmol) in dry CCl4 (5 mL) was stirred and heated to reflux for 3 h. After cooling, the mixture-was filtered, and the red filtrate was washed with a saturated solution of sodium thiosulfate (2×10 mL). The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel (petroleum ether), to give 60 as a white solid (361 mg, 55%). 1H NMR (CDCl3, 300 MHz) δ 7.76 (d, J=2.4 Hz, 1H), 7.56 (dd, J=8.7, 2.1 Hz, 1H), 7.12 (d, J=8.4 Hz, 1H), 4.49 (s, 2H). MS (m/e) (positive FAB) 332.1 (M+H)+, m.p. 94-95° C.

후처리

  1. temperatureheated
  2. temperatureto reflux for 3 h
  3. temperatureAfter cooling
  4. filtrationthe mixture-was filtered
  5. washthe red filtrate was washed with a saturated solution of sodium thiosulfate (2×10 mL)
  6. washThe organic phase was washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by flash chromatography on silica gel (petroleum ether)

출처 및 근거

ORD 기록
ord-f299178d776541c5a4c6e0eed6c6f40e
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07825126B2

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