Water → HCID 21852285, compound

HRID 617436Notes

Reaction equation

HRID 617436 reaction equation
[Cl:1][C:2]1[CH:8]=[C:6]([OH:7])[C:5]([OH:9])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[C:13]([O-])([O-])=O.[K+].[K+].C(Br)Br.O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[C:5]2[O:9][CH2:13][O:7][C:6]=2[CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3024DibromomethaneHCID 11430Potassium CarbonateHCID 21852281HCID 21852281, compound

Product 1

HCID 21852285HCID 21852285, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

Under N2 200 g of 5-chloro-3-nitro-catechol is dissolved in 1050 ml DMF. To this solution are added 204 g anhydrous, powdered K2CO3 and 220 ml CH2Br2, while stirring the mixture. The reaction mixture is refluxed for 1 hour (140° C.) and then cooled down to 80° C. After addition of 800 ml water, the mixture is cooled down to room temp. The crystalline product is filtered off and washed successively with 2×600 ml water, 2×250 ml ethanol, and 2×300 ml n-hexane. After drying under reduced pressure at 60° C., the desired product is obtained in a yield of 82%; purity 95%. Equally successful results are obtained in toluene as the solvent instead of DMF, under phase transfer conditions.

Workup

  1. additionTo this solution are added 204 g anhydrous
  2. temperaturecooled down to 80° C
  3. temperaturethe mixture is cooled down to room temp
  4. filtrationThe crystalline product is filtered off
  5. washwashed successively with 2×600 ml water, 2×250 ml ethanol, and 2×300 ml n-hexane
  6. customAfter drying under reduced pressure at 60° C.

Sources & evidence

ORD record
ord-ec6525f1238f473bb6db505f23750031
Source dataset
uspto-grants-1999_09
Patent number
US05948909

Reaction notes

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