Ethanol → HCID 59398782, compound

HRID 1669220Notes

Reaction equation

HRID 1669220 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8](=O)[CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Br:18])[CH:13]=2)[CH3:11])[CH:5]=[CH:6][CH:7]=1.[Cl:20][C:21]1[CH:22]=[C:23]([C:27](=O)[CH3:28])[CH:24]=[CH:25][CH:26]=1.C(O)C.[Si](Cl)(Cl)(Cl)Cl>O>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:28]=[C:27]([C:23]3[CH:24]=[CH:25][CH:26]=[C:21]([Cl:20])[CH:22]=3)[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([Br:18])[CH:13]=3)[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 149331-(3-Chlorophenyl)ethanoneHCID 24816Silicon tetrachlorideHCID 671447791,3-Bis(3-bromophenyl)but-2-en-1-one

Product 1

HCID 59398782HCID 59398782, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1,3-bis(3-bromophenyl)but-2-en-1-one (6.15 g, 16.2 mmol) and m-chloroacetophenone (2.50 g, 16.2 mmol) were added to a 100 mL of three neck round bottom flask. To this flask, dry ethanol (40 mL) was added. The mixture was stirred vigorously, and then silicon tetrachloride (7 ml, 56 mmol) was added slowly. The mixture turned red and stirred 12 hours at room temperature. Then water (10 ml×2) was added and stirred for 20 minutes. Then filter the solution to get grey solid. Washed the solid with NaOH solution (10%), water and acetone separately. Dried the crude product and dissolved in THF (3 ml), then added the THF solution to methanol (100 ml) under stirring vigorously. Get the precipitation by filtration, and then recrystallize the crude product from ethanol and dichloromethane, the fine 1,3-Bis(3-bromophenyl)-5-(3-chlorophenyl) benzene will be obtained. Yield is 3.23 g (C24H15Br2Cl), 40%. 1H NMR (δ, CDCl3) 7.84 (m, 2H), 7.74 (m, 3H), 7.69 (s, 1H), 7.63-7.55 (m, 5H), 7.46-7.36 (m, 4H).

Workup

  1. stirringstirred 12 hours at room temperature
  2. stirringstirred for 20 minutes
  3. filtrationThen filter the solution
  4. customto get grey solid
  5. washWashed the solid with NaOH solution (10%), water and acetone separately
  6. dry with materialDried the crude product
  7. dissolutiondissolved in THF (3 ml)
  8. additionadded the THF solution to methanol (100 ml)
  9. stirringunder stirring vigorously
  10. customGet
  11. customthe precipitation
  12. filtrationby filtration
  13. customrecrystallize the crude product from ethanol and dichloromethane

Sources & evidence

ORD record
ord-074ff8e40d9447279481144828f407e2
Source dataset
uspto-grants-2011_08
Patent number
US07989476B2

Reaction notes

Loading…