Hydrochloric Acid → HCID 59516842, compound

HRID 1161464Notes

Reaction equation

HRID 1161464 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 reaction mixture 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 reaction mixture 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-d1e3ab85fd56427cab61fe232a3c7e62
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

Loading…