1,2-Dimethoxyethane → Methyl 5-(4-fluoro-2-methylphenyl)-2-(methoxymethyl)furan-3-carboxylate

HRID 1877103Notes

Reaction equation

HRID 1877103 reaction equation
Br[C:2]1[O:6][C:5]([CH2:7][O:8][CH3:9])=[C:4]([C:10]([O:12][CH3:13])=[O:11])[CH:3]=1.[F:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[C:17]([CH3:24])[CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+].COCCOC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[F:14][C:15]1[CH:20]=[CH:19][C:18]([C:2]2[O:6][C:5]([CH2:7][O:8][CH3:9])=[C:4]([C:10]([O:12][CH3:13])=[O:11])[CH:3]=2)=[C:17]([CH3:24])[CH:16]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 2734665(4-Fluoro-2-methylphenyl)boronic acidHCID 68509863Methyl 5-bromo-2-(methoxymethyl)-3-furancarboxylate

Product 1

HCID 68514123Methyl 5-(4-fluoro-2-methylphenyl)-2-(methoxymethyl)furan-3-carboxylateYield 93.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

A mixture of methyl 5-bromo-2-(methoxymethyl)-3-furancarboxylate (2.5 g), 4-fluoro-2-methylphenylboronic acid (1.9 g), tetrakis(triphenylphosphine)palladium(0) (0.6 g), 2N aqueous sodium carbonate solution (12 mL) and 1,2-dimethoxyethane (20 mL) was stirred under reflux overnight under an argon atmosphere. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (0% ethyl acetate/hexane to 20% ethyl acetate/hexane) to give the title compound (2.6 g, 92%) as an oil.

Workup

  1. temperatureunder reflux overnight under an argon atmosphere
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (0% ethyl acetate/hexane to 20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-105d42f39974402aae07968b54dc3fdc
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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