Water → HCID 86052306, compound

HRID 1782037Notes

Reaction equation

HRID 1782037 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[C:5]([OH:6])=[CH:4][C:3]=1[OH:10].C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][C:19]([O:21][CH3:22])=[O:20].O>CN(C=O)C>[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[C:5]([OH:6])=[CH:4][C:3]=1[O:10][CH2:18][C:19]([O:21][CH3:22])=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 672994,6-Dichloro-1,3-benzenediol

Product 1

HCID 86052306HCID 86052306, compoundYield 23.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4,6-dichlororesorcinol (2 g), potassium carbonate (1.54 g) and methyl bromoacetate (1.71 g) in DMF (10 ml) was heated at 80° C. for 24 h. The resulting mixture was cooled and water (200 ml) added. Solid (bis-alkylated product) was filtered off, then the aqueous was acidified with aq. HCl, which was extracted with ether and the organics were dried and concentrated in vacuo. Purification by RPHPLC (Xterra, gradient 95-5%, ammonia (0.2% aq.) in acetonitrile) gave the subtitle compound (0.65 g) as a solid.

Workup

  1. temperatureThe resulting mixture was cooled
  2. filtrationSolid (bis-alkylated product) was filtered off
  3. extractionwas extracted with ether
  4. customthe organics were dried
  5. concentrationconcentrated in vacuo
  6. customPurification by RPHPLC (Xterra, gradient 95-5%, ammonia (0.2% aq.) in acetonitrile)

Sources & evidence

ORD record
ord-f3955082ebdf49f99c8913127af764d7
Source dataset
uspto-grants-2009_03
Patent number
US07498338B2

Reaction notes

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