1,2-Dibromoethane → HCID 17906318, compound

HRID 852084Notes

Reaction equation

HRID 852084 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]2[C:6]([C:9]3[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=3)=[N:7][O:8][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Br:24][CH2:25][CH2:26]Br>C(OCC)(=O)C>[Br:24][CH2:25][CH2:26][O:15][C:12]1[CH:11]=[CH:10][C:9]([C:6]2[C:5]3[CH:16]=[CH:17][C:2]([F:1])=[CH:3][C:4]=3[O:8][N:7]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 136158584HCID 136158584, compound

Product 1

HCID 17906318HCID 17906318, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Combine 4-(6-fluoro-benzo[d]isoxazol-3-yl)-phenol (2.00 g, 8.726 mmol) and potassium carbonate (1.81 g, 13.088 mmol) in 1,2-dibromoethane (9.70 mL) and heat at reflux for 6 hours. Cool reaction mixture to room temperature and dilute with ethyl acetate (150 mL) and wash with water (50 mL), 10% HCl (50 mL), water (50 mL), saturated sodium chloride (50 mL), dry (MgSO4), filter and evaporate. Purify the residue by column chromatography (5% ethyl acetate in heptane) to obtain the title compound as a white solid (1.21 g, 41% Yield).

Workup

  1. temperatureat reflux for 6 hours
  2. temperatureCool
  3. customreaction mixture to room temperature
  4. washwash with water (50 mL), 10% HCl (50 mL), water (50 mL), saturated sodium chloride (50 mL)
  5. dry with materialdry (MgSO4)
  6. filtrationfilter
  7. customevaporate
  8. customPurify the residue by column chromatography (5% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-35e18b70f26443f290778c24c3f60620
Source dataset
uspto-grants-2007_08
Patent number
US07253165B2

Reaction notes

Loading…