Hydrochloric Acid → HCID 59516842, compound

HRID 1698714Notes

Reaction equation

HRID 1698714 reaction equation
Br[CH2:2][CH2:3][CH2:4]Br.C(=O)([O-])[O-].[K+].[K+].[Br:12][C:13]1[C:14]([F:23])=[C:15]([OH:22])[C:16]([OH:21])=[C:17]([O:19][CH3:20])[CH:18]=1.Cl>CN(C=O)C>[Br:12][C:13]1[CH:18]=[C:17]([O:19][CH3:20])[C:16]2[O:21][CH2:2][CH2:3][CH2:4][O:22][C:15]=2[C:14]=1[F:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 59517296HCID 59517296, compound

Product 1

HCID 59516842HCID 59516842, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

After adding 830 mg of 1,3-dibromopropane and 1.4 g of potassium carbonate to a solution of 880 mg of 4-bromo-3-fluoro-6-methoxybenzene-1,2-diol (Example (41a)) in 10 ml of DMF, the mixture was stirred at 80° C. for 6 hours. After adding 1N hydrochloric acid to the reaction mixture, 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 (548 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-3d18756075d5459baca873704f1721ba
Source dataset
uspto-grants-2012_04
Patent number
US08163787B2

Reaction notes

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