Methanol → 1-[4-(4-Bromo-2-fluorobenzyloxy)-2-hydroxyphenyl]ethanone

HRID 2192701Notes

Reaction equation

HRID 2192701 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].[Br:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19]Br)=[C:15]([F:21])[CH:14]=1.C(=O)([O-])[O-].[K+].[K+].CO>CN(C=O)C.O>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][O:8][C:6]2[CH:5]=[CH:4][C:3]([C:9](=[O:11])[CH3:10])=[C:2]([OH:1])[CH:7]=2)=[C:15]([F:21])[CH:14]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 69902',4'-DihydroxyacetophenoneHCID 11430Potassium Carbonate2×HCID 27336604-Bromo-2-fluorobenzyl bromide

Product 1

HCID 669882381-[4-(4-Bromo-2-fluorobenzyloxy)-2-hydroxyphenyl]ethanoneYield 75.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1-(2,4-dihydroxyphenyl)ethanone (25.3 g, 0.17 mol) and 4-bromo-1-bromomethyl-2-fluorobenzene (44.6 g, 0.17 mol) were dissolved in DMF (150 mL). Potassium carbonate (11.8 g, 0.09 mol) was added to the solution under ice-cooled conditions, and the mixture was stirred under ice-cooled conditions and further stirred at room temperature for 12 hours. Again, potassium carbonate (11.8 g, 0.09 mol) was added to the mixture under ice-cooled conditions, and the mixture was stirred under ice-cooled conditions for 30 minutes and further stirred at room temperature for 12 hours. Methanol (100 mL) was added to this reaction solution, and the mixture was stirred at 80° C. for 1 hour. Thereafter, water (150 mL) was added to the mixture, and precipitated crystals were filtered and washed with methanol. The crystals were vacuum-dried at 60° C. for 2 hours, yielding 1-[4-(4-bromo-2-fluorobenzyloxy)-2-hydroxyphenyl]ethanone (43.5 g, yield: 75%).

Workup

  1. temperaturecooled conditions
  2. temperaturecooled conditions
  3. stirringfurther stirred at room temperature for 12 hours
  4. temperaturecooled conditions
  5. stirringthe mixture was stirred under ice-
  6. temperaturecooled conditions for 30 minutes
  7. stirringfurther stirred at room temperature for 12 hours
  8. stirringthe mixture was stirred at 80° C. for 1 hour
  9. customprecipitated crystals
  10. filtrationwere filtered
  11. washwashed with methanol
  12. customThe crystals were vacuum-dried at 60° C. for 2 hours

Sources & evidence

ORD record
ord-007942aad0dc467980dae15584f6932f
Source dataset
uspto-grants-2012_12
Patent number
US08329739B2

Reaction notes

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