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

HRID 1716970Notes

Reaction equation

HRID 1716970 reaction equation
[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]

Participants

3

Reactant 2

HCID 1140Toluene2×HCID 590134742-Bromo-5-chloro-4-(4-ethylbenzyl)benzaldehyde

Product 1

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

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-e2592b3ed9674412923235a09c29482a
Source dataset
uspto-grants-2010_09
Patent number
US07803778B2

Reaction notes

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