Dimethylformamide → HCID 86666827, compound

HRID 510910Notes

Reaction equation

HRID 510910 reaction equation
[Br:1][C:2]1[C:3]([OH:13])=[C:4]([C:10](=[O:12])[CH3:11])[CH:5]=[C:6]([F:9])[C:7]=1[CH3:8].[C:14](=O)([O-])[O-].[K+].[K+].CN(C)C=O.CI>O>[Br:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([C:10](=[O:12])[CH3:11])[CH:5]=[C:6]([F:9])[C:7]=1[CH3:8]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 86666826HCID 86666826, compound

Product 1

HCID 86666827HCID 86666827, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 1-(3-bromo-5-fluoro-2-hydroxy-4-methylphenyl)ethanone (0.3 g, 1 mmol) and potassium carbonate (0.43 g, 3.1 mmol) was added N,N-dimethylformamide (1 mL) and methyl iodide (0.17 mL, 2.7 mmol) with stirring. The resulting mixture was then heated at 60° C. for 1 hour. The mixture was diluted with water and extracted with ethyl acetate. The combined extracts were washed with brine, dried over sodium sulfate, and evaporated to dryness. The isolated residue was purified on silica gel, eluting with ethyl acetate/hexanes (0 to 20%) to yield 1-(3-Bromo-5-fluoro-2-methoxy-4-methylphenyl)ethanone (0.24 g, 80%). LCMS calculated for C10H11BrFO2 (M+H)+: m/z=261.0, 263.0. Found: 260.9, 262.9. 1H NMR (400 MHz, CDCl3): δ 7.35 (m, 1H), 3.82 (s, 3H), 2.61 (s, 3H), 2.39 (s, 3H).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness
  5. customThe isolated residue was purified on silica gel
  6. washeluting with ethyl acetate/hexanes (0 to 20%)

Sources & evidence

ORD record
ord-e103d5b8665140479d2b083d4b7b51e8
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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