Water → Ethyl 2'-fluoro-5'-methoxy-4-((4-methoxybenzyl)oxy)biphenyl-2-carboxylate

HRID 1049555Notes

Reaction equation

HRID 1049555 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[C:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=1.[CH3:22][O:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Cl)=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[C:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:12][C:13]([O:16][CH2:28][C:27]2[CH:30]=[CH:31][C:24]([O:23][CH3:22])=[CH:25][CH:26]=2)=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 117759944Ethyl 2'-fluoro-4-hydroxy-5'-methoxy-[1,1'-biphenyl]-2-carboxylate

Product 1

HCID 117759585Ethyl 2'-fluoro-5'-methoxy-4-((4-methoxybenzyl)oxy)biphenyl-2-carboxylateYield 99.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of ethyl 2′-fluoro-4-hydroxy-5′-methoxy-[1,1′-biphenyl]-2-carboxylate (15.84 g), 4-methoxybenzyl chloride (17.09 g) and potassium carbonate (18.85 g) in DMF (110 mL) was stirred at room temperature for 14 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (22.3 g) as a pale-yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a2d8447a5d034b13a83b9e4abb8917bd
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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