Water → HCID 86612235, compound

HRID 30054Notes

Reaction equation

HRID 30054 reaction equation
[CH:1]([C:3]1[C:12](OS(C(F)(F)F)(=O)=O)=[CH:11][C:10]([O:21][CH3:22])=[CH:9][C:4]=1[C:5]([O:7]C)=[O:6])=[O:2].[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C1(C)C=CC=CC=1.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.[Pd]>[CH:1]([C:3]1[C:12]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:11][C:10]([O:21][CH3:22])=[CH:9][C:4]=1[C:5]([OH:7])=[O:6])=[O:2]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 86612236HCID 86612236, compound

Product 1

HCID 86612235HCID 86612235, compound

Reagents, catalysts & solvents 2

HCID 178527696HCID 178527696, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A solution of about 2.3 mmol of methyl 2-formyl-5-methoxy-3-trifluoromethanesulfonyloxybenzoate in 10 mL of toluene is stirred under argon, and 330 mg (2.7 mmol) of phenylboronic acid, 84 mg of tetrakis palladium and 2.5 mL of aqueous 2N sodium carbonate solution are added. The mixture is stirred at 110° C. for 6 hours in a stoppered tube under argon. Water is added to the cooled reaction medium, and the mixture is washed with ethyl acetate and, after acidification (1N HCl), is then extracted with dichloromethane. The organic phase is dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The product, in the form of a brown solid, is used without purification in the following reaction.

Workup

  1. washthe mixture is washed with ethyl acetate
  2. extractionafter acidification (1N HCl), is then extracted with dichloromethane
  3. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe product, in the form of a brown solid, is used without purification in the following reaction

Sources & evidence

ORD record
ord-38611fe270de45ee8c2a7067d35e6e2d
Source dataset
uspto-grants-2008_09
Patent number
US07423030B2

Reaction notes

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