1,1-Dibromoethane → HCID 69031119, compound

HRID 1868608Notes

Reaction equation

HRID 1868608 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([O:14][C:15]1[CH:16]=[C:17]([CH:30]=[C:31]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:32]=1)[C:18]1[O:19][C:20]2[C:25]([C:26](=[O:28])[CH:27]=1)=[CH:24][CH:23]=[C:22]([OH:29])[CH:21]=2)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Br:41][CH:42](Br)[CH3:43]>CN(C)C=O>[Br:41][CH2:42][CH2:43][O:29][C:22]1[CH:21]=[C:20]2[C:25]([C:26](=[O:28])[CH:27]=[C:18]([C:17]3[CH:16]=[C:15]([O:14][CH2:7][C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=4)[CH:32]=[C:31]([O:33][CH2:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[CH:30]=3)[O:19]2)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 112011,1-DibromoethaneHCID 11430Potassium CarbonateHCID 58209852HCID 58209852, compound2×

Product 1

HCID 69031119HCID 69031119, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (2.76 g, 20 mmol) was added to a stirred solution of 3′,5′-dibenzyloxy-7-hydroxy-flavone, 22 (2.25 g, 5 mmol) in dry dimethyl formamide (120 mL). After the mixture was stirred for 30 min, dibromo ethane (5 mL, 58 mmol) was added and the resultant was stirred at room temperature for 12 h. Reaction mixture was filtered through celite, concentrated under reduced pressure and extracted with chloroform. The extract was washed with water, dried over sodium sulphate, filtered and concentrated in vacuo. The residue was purified by column chromatography to afford 56.

Workup

  1. stirringthe resultant was stirred at room temperature for 12 h
  2. customReaction mixture
  3. filtrationwas filtered through celite
  4. concentrationconcentrated under reduced pressure
  5. extractionextracted with chloroform
  6. washThe extract was washed with water
  7. dry with materialdried over sodium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-75660f8642944b1aad88a5f44b92adc6
Source dataset
uspto-grants-2009_12
Patent number
US07635779B2

Reaction notes

Loading…