Acetovanillone → HCID 43384906, compound

HRID 2192700Notes

Reaction equation

HRID 2192700 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[O:11][CH3:12].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.[Br:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31]Br)=[C:27]([F:33])[CH:26]=1>O.CO>[Br:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][O:1][C:2]2[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=2[O:11][CH3:12])=[C:27]([F:33])[CH:26]=1

Participants

7

Reactant 4

HCID 2214AcetovanilloneHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 27336604-Bromo-2-fluorobenzyl bromide

Product 1

HCID 43384906HCID 43384906, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

1-(4-hydroxy-3-methoxyphenyl)ethanone (25.0 g, 0.15 mol) and potassium carbonate (15.4 g, 0.11 mol) were added to DMF (80 mL). 4-bromo-1-(bromomethyl)-2-fluorobenzene (50.2 g, 0.19 mol) was added to the mixture, and the mixture was stirred at room temperature for 2 hours and then stirred at 60° C. for 16 hours. Methanol (40 mL) was added to this reaction solution, which was stirred at 60° C. for 1 hour and then blended with water (200 mL). The precipitated crystals were filtered and washed with water and hexane. The crystals were vacuum-dried at 60° C. for 3 hours, yielding 1-[4-(4-bromo-2-fluorobenzyloxy)-3-methoxyphenyl]ethanone (52.7 g).

Workup

  1. stirringstirred at 60° C. for 16 hours
  2. stirringwas stirred at 60° C. for 1 hour
  3. filtrationThe precipitated crystals were filtered
  4. washwashed with water and hexane
  5. customThe crystals were vacuum-dried at 60° C. for 3 hours

Sources & evidence

ORD record
ord-ecaf21876803469fb9a756968a3c0735
Source dataset
uspto-grants-2012_12
Patent number
US08329739B2

Reaction notes

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