Water → HCID 60143708, compound

HRID 337338Notes

Reaction equation

HRID 337338 reaction equation
C[O:2][C:3]1[CH:8]=[C:7]([O:9]C)[CH:6]=[CH:5][C:4]=1[N:11]1[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[N:12]1.B(Br)(Br)Br.O.[OH-].[Na+]>C(Cl)Cl>[CH3:17][C:13]1[CH:14]=[C:15]([CH3:16])[N:11]([C:4]2[CH:5]=[CH:6][C:7]([OH:9])=[CH:8][C:3]=2[OH:2])[N:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 39248127HCID 39248127, compound

Product 1

HCID 60143708HCID 60143708, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

118.4 mg of 1-(2,4-dimethoxyphenyl)-3,5-dimethyl-1H-pyrazol was dissolved in 2.3 ml of methylene chloride, and 1.7 ml of 1M solution of boron tribromide in methylene chloride was added at room temperature and stirred for 1 hour. The reaction mixture was added to 30 ml of water, neutralized with 1N-sodium hydroxide, and extracted with 50 ml of ethyl acetate. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and purified using preparative thin-layer silica gel column chromatography (hexane:ethyl acetate=1:2) to yield 71.7 mg of the title compound.

Workup

  1. extractionextracted with 50 ml of ethyl acetate
  2. dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. custompurified

Sources & evidence

ORD record
ord-26b80433f92546c3adca80079702c3ec
Source dataset
uspto-grants-2014_11
Patent number
US08889727B2

Reaction notes

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