1,1-Dibromoethane → HCID 22994352, compound

HRID 1167819Notes

Reaction equation

HRID 1167819 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:28])[O:10][C:11]3[C:16]([C:17]=2[CH2:18][C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=2)=[CH:15][CH:14]=[C:13]([O:26][CH3:27])[CH:12]=3)=[CH:4][CH:3]=1.[Br:29][CH:30](Br)[CH3:31].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9](=[O:28])[O:10][C:11]3[C:16]([C:17]=2[CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:31][CH2:30][Br:29])=[CH:21][CH:20]=2)=[CH:15][CH:14]=[C:13]([O:26][CH3:27])[CH:12]=3)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 112011,1-DibromoethaneHCID 11430Potassium CarbonateHCID 22994357HCID 22994357, compound

Product 1

HCID 22994352HCID 22994352, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 3-(4-chlorophenyl)-4-(4-hydroxybenzyl)-7-methoxychromen-2-one (21.2 g, 54 mmol), dibromoethane (50.7 g, 270 mmol), and K2CO3 (8.3 g, 60 mmol) in 200 mL of acetone was heated at reflux for 12 h. The reaction mixture was cooled to room temperature and volatiles were removed under reduced pressure. Hexanes (500 mL) was added with stirring and the resulting solid that formed was collected by filtration. The material was rinsed with hexanes (2×100 mL), collected and dried under vacuum to provide the desired product (22.5 g, 83%). 1H NMR (300 MHz, DMSO) δ 7.50 (d, 1H, J=9.1 Hz), 7.48 (d, 2H, J=8.2 Hz), 7.35 (d, 2H, J=8.2 Hz), 7.07 (d, 2H, J=8.5 Hz), 7.04 (d, 1H, J=2.6 Hz), 6.86 (dd, 1H, J=9.1, 2.6Hz), 6.82 (d, 2H, J=8.5 Hz), 4.24 (t, 2H, J=5.8 Hz), 3.98 (s, 2H), 3.84 (s, 3H), 3.76 (t, 2H, J=5.8 Hz). MS (ESI) m/z 500 (M+H)+.

Workup

  1. temperatureat reflux for 12 h
  2. customvolatiles were removed under reduced pressure
  3. additionHexanes (500 mL) was added
  4. customthe resulting solid that formed
  5. filtrationwas collected by filtration
  6. washThe material was rinsed with hexanes (2×100 mL)
  7. customcollected
  8. customdried under vacuum

Sources & evidence

ORD record
ord-a2eda0ee73144be98db941ea0134d68c
Source dataset
uspto-grants-2003_09
Patent number
US06620838B1

Reaction notes

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