2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 21911878, compound

HRID 2217175Notes

Reaction equation

HRID 2217175 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[OH:10].[F:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>CO>[F:11][C:12]1[CH:19]=[CH:18][C:15]([C:16]2[O:10][C:3]3[CH:4]=[CH:5][C:6]([O:8][CH3:9])=[CH:7][C:2]=3[N:1]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 680234-FluorobenzaldehydeHCID 14191082-Amino-4-methoxyphenol

Product 1

HCID 21911878HCID 21911878, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 2-amino-4-methoxyphenol (3.07 g, 22.09 mmol) and 4-fluorobenzaldehyde (3.55 mL, 33.14 mmol) in 40 mL of methanol was stirred at 45° C. overnight. The solvent was evaporated under reduced pressure, and the residue was dissolved in methylene chloride (50 mL), to which was added DDQ (6.02 g, 26.51 mmol) slowly. The resulting mixture was stirred at room temperature for 45 minutes. The solvent was evaporated under reduced pressure, and to the residue was added 300 mL of ethyl acetate. The organic layer was washed sequentially with saturated sodium bicarbonate and brine, dried over sodium sulfate, and evaporated under reduced pressure. Column chromatography (ethyl acetate:Hexanes=1:9) gave 2-(4-fluorophenyl)-5-methoxybenzoxazole as a white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in methylene chloride (50 mL), to which
  3. stirringThe resulting mixture was stirred at room temperature for 45 minutes
  4. customThe solvent was evaporated under reduced pressure
  5. additionto the residue was added 300 mL of ethyl acetate
  6. washThe organic layer was washed sequentially with saturated sodium bicarbonate and brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-441610331d774c91a887f4226bd3a50d
Source dataset
uspto-grants-2008_08
Patent number
US07407960B2

Reaction notes

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