Dimethylformamide → 1-(4-Bromo-2-methoxyphenyl)ethan-1-one

HRID 1993769Notes

Reaction equation

HRID 1993769 reaction equation
IC.[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[C:6]([OH:13])[CH:5]=1.[CH3:14]N(C=O)C.C(=O)([O-])[O-].[K+].[K+]>O>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[C:6]([O:13][CH3:14])[CH:5]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 107274031-(4-Bromo-2-hydroxyphenyl)ethan-1-one

Product 1

HCID 112184481-(4-Bromo-2-methoxyphenyl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Iodomethane (11.2 mL) was added to a mixture of compound 6b (32.6 g), DMF (100 mL), and potassium carbonate (62.5 g) at 0° C. The mixture was stirred and allowed to warm to RT over 2 hr. Water (200 mL) was added, and the mixture was extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate, filtered, and evaporated to afford 1-(4-bromo-2-methoxyphenyl)-1-ethanone (compound 6c, 33.1 g) as a tan solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-87032146984b4d9f8c10e1aa1eaa4157
Source dataset
uspto-grants-2010_01
Patent number
US07652035B2

Reaction notes

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