Toluene → 1-Bromo-4-chloro-5-(4-ethylbenzyl)-2-vinylbenzene

HRID 1716970노트

반응식

HRID 1716970 반응식
[Br:1][C:2]1[CH:9]=[C:8]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH3:18])=[CH:13][CH:12]=2)[C:7]([Cl:19])=[CH:6][C:3]=1[CH:4]=O.[C:20]1(C)C=CC=CC=1>>[Br:1][C:2]1[CH:9]=[C:8]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH3:18])=[CH:13][CH:12]=2)[C:7]([Cl:19])=[CH:6][C:3]=1[CH:4]=[CH2:20]

참가 물질

3

반응물 2

HCID 1140Toluene2회HCID 590134742-Bromo-5-chloro-4-(4-ethylbenzyl)benzaldehyde

생성물 1

HCID 590134581-Bromo-4-chloro-5-(4-ethylbenzyl)-2-vinylbenzene

실험 절차

To a suspension of Ph3PCH3I (3.151 g, 7.8 mmol) in 22 mL of dry toluene, was added dropwise with KN(TMS)2 (15.64 mL, 7.8 mmol, 0.5 M in toluene) under argon. After it was stirred for 1 h, a solution of 2-bromo-5-chloro-4-(4-ethylbenzyl)benzaldehyde (1.76 g, 5.2 mmol) in 17 mL of toluene was added. This reaction mixture was stirred at room temperature and monitored by TLC (PE, Rf=0.8). After being stirred for 4 h, the reaction mixture was quenched by addition of 5 mL of saturated NaHCO3. The organic layer was washed 2× with H2O, 2× with brine, dried over anhydrous Na2SO4. Concentration under reduced pressure provided the crude product, which was purified by column chromatography on silica gel (PE), to give the title compound as a colorless oil. Yield: 3.0 g (96%). 1H NMR (CDCl3, 300 MHz) δ 7.54 (s, 1H), 7.33 (s, 1H), 7.14 (d, J=2.1 Hz, 1H), 7.12 (d, J=2.4 Hz, 1H), 7.10 (d, J=2.1 Hz, 1H), 7.09 (d, J=2.4 Hz, 1H), 6.92 (dd, J=11.0, 17.6 Hz, 1H), 5.68 (dd, J=17.6, 0.9 Hz, 1H), 5.37 (dd, J=11.0, 0.9 Hz, 1H), 4.02 (s, 2H), 2.63 (q, J=7.6 Hz, 2H), 1.23 (t, J=7.6 Hz, 3H).

후처리

  1. additionwas added dropwise with KN(TMS)2 (15.64 mL, 7.8 mmol, 0.5 M in toluene) under argon
  2. stirringThis reaction mixture was stirred at room temperature
  3. stirringAfter being stirred for 4 h
  4. customthe reaction mixture was quenched by addition of 5 mL of saturated NaHCO3
  5. washThe organic layer was washed 2× with H2O, 2× with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationConcentration under reduced pressure
  8. customprovided the crude product, which
  9. customwas purified by column chromatography on silica gel (PE)

출처 및 근거

ORD 기록
ord-e2592b3ed9674412923235a09c29482a
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07803778B2

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