Sodium Carbonate → HCID 68537012, compound

HRID 1985038Notes

Reaction equation

HRID 1985038 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6](OS(C(F)(F)F)(=O)=O)=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])[CH3:2].[F:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CCO.CCOCC.O.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>[CH2:1]([C:3]1[CH:12]=[C:7]([C:8]([O:10][CH3:11])=[O:9])[C:6]([C:25]2[CH:26]=[CH:27][C:22]([F:21])=[CH:23][CH:24]=2)=[CH:5][CH:4]=1)[CH3:2]

Participants

9

Reactant 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 60206812Benzoic acid, 5-ethyl-2-[[(trifluoromethyl)sulfonyl]oxy]-, methyl ester

Product 1

HCID 68537012HCID 68537012, compound

Reagents, catalysts & solvents 5

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
90 °C

Procedure

To 1.5 g (4.8 mmol) of product from Step 1 in 12.5 mL of toluene at room temperature was added 0.28 g (0.24 mmol, 0.05 eq.) of Pd(PPh3)4. After stirring for 5 min, 1.1 g (5.7 mmol, 1.2 eq.) of 4-fluorophenylboronic acid in 5.5 mL of EtOH followed by 11.5 mL of 2 M aqueous Na2CO3 were added. After heating at 90° C. for 12 h the reaction was judged complete, cooled and diluted with Et2O (100 mL) and water (50 mL). The resulting layers were separated and the aqueous layer extracted twice with Et2O (100 mL). The combined organic layers are dried over MgSO41 filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography to yield the desired methyl 4-ethyl-4′-fluoro-1,1′-biphenyl-2-carboxylate. C16H15O2F+H+ requires 258 found 258.

Workup

  1. additionwere added
  2. temperaturecooled
  3. customThe resulting layers were separated
  4. extractionthe aqueous layer extracted twice with Et2O (100 mL)
  5. customThe combined organic layers are dried over MgSO41
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-22ca1003c4d7441b97649dc8110039c0
Source dataset
uspto-grants-2009_06
Patent number
US07544717B2

Reaction notes

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