Hydrochloric Acid → HCID 59517200, compound

HRID 1698710Notes

Reaction equation

HRID 1698710 reaction equation
Br[CH2:2][CH2:3]Br.C(=O)([O-])[O-].[K+].[K+].[Br:11][C:12]1[C:13]([F:22])=[C:14]([OH:21])[C:15]([OH:20])=[C:16]([O:18][CH3:19])[CH:17]=1.Cl>CN(C=O)C>[Br:11][C:12]1[CH:17]=[C:16]([O:18][CH3:19])[C:15]2[O:20][CH2:2][CH2:3][O:21][C:14]=2[C:13]=1[F:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 59517296HCID 59517296, compound

Product 1

HCID 59517200HCID 59517200, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

After adding 830 mg of 1,2-dibromoethane and 1.4 g of potassium carbonate to a solution of 880 mg of 4-bromo-3-fluoro-6-methoxybenzene-1,2-diol in 10 ml of DMF, the mixture was stirred at 80° C. for 6 hours. Next, 1N hydrochloric acid was added to the reaction mixture and the organic layer was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate-heptane) to give the title compound (549 mg) as a solid.

Workup

  1. extractionthe organic layer was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationThe desiccating agent was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by NH silica gel column chromatography (ethyl acetate-heptane)

Sources & evidence

ORD record
ord-7c8ab60f399645b48384075cddb68710
Source dataset
uspto-grants-2012_04
Patent number
US08163787B2

Reaction notes

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