Potassium Carbonate → HCID 86731303, compound

HRID 2277231Notes

Reaction equation

HRID 2277231 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:11][CH3:12])[C:9]=1[OH:10])[CH:5]=[O:6].C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][CH:21]1[CH2:23][CH2:22]1>CN(C=O)C.C(OCC)(=O)C>[CH:21]1([CH2:20][O:10][C:9]2[C:8]([O:11][CH3:12])=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=2[F:1])[CH2:23][CH2:22]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 5984523-Fluoro-4-hydroxy-5-methoxybenzaldehyde

Product 1

HCID 86731303HCID 86731303, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 3-fluoro-4-hydroxy-5-methoxybenzaldehyde (5.00 g) in DMF (50 mL) were added potassium carbonate (6.09 g) and (bromomethyl)cyclopropane (3.42 mL), and the mixture was stirred with heating at 70° C. for 1 hr. The reaction mixture was allowed to cool to room temperature, diluted with ethyl acetate, and washed with saturated brine. The obtained organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (6.59 g).

Workup

  1. temperatureto cool to room temperature
  2. washwashed with saturated brine
  3. dry with materialThe obtained organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-b128083f43674d5bb968a3a1b5bb2569
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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