Dimethylformamide → HCID 22734079, compound

HRID 1057925Notes

Reaction equation

HRID 1057925 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][CH3:10])=[C:6]([OH:8])[CH:7]=1.Cl[CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][C:13]1=[O:18].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][CH3:10])=[C:6]([O:8][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]2=[O:18])[CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 132032-ChlorocyclohexanoneHCID 1422285-Bromo-2-methoxyphenol

Product 1

HCID 22734079HCID 22734079, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 5-bromo-2-methoxyphenol (120.0 g), 2-chloro-1-cyclohexanone (108.0 g), potassium carbonate (163.3 g), and DMF (1.2 l) was stirred at 70° C. for 3 hours. After being allowed to stand for cooling, water was added to the mixture followed by extraction with ethyl acetate. The organic layer was washed with a saturated saline and dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to give Compound IId-a (138.5 g, 78.3%) as pale-yellow crystals.

Workup

  1. temperaturefor cooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with a saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)
  7. customto give Compound IId-a (138.5 g, 78.3%) as pale-yellow crystals

Sources & evidence

ORD record
ord-5a90e2e110e24445876d4eba98b6e822
Source dataset
uspto-grants-2003_02
Patent number
US06514996B2

Reaction notes

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