Water → HCID 22172943, compound

HRID 1062926Notes

Reaction equation

Cl[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[CH:8]([CH3:12])[CH2:7]2.[CH3:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C(O)CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:12][CH:8]1[CH2:7][C:6]2[C:10](=[C:2]([C:17]3[CH:18]=[CH:19][C:14]([CH3:13])=[CH:15][CH:16]=3)[CH:3]=[CH:4][CH:5]=2)[C:9]1=[O:11]

Participants

Conditions

Temperature: 125 °C

Procedure

Using a method similar to Example 16 d), 3.61 g (0.020 mol) of (1), 3.0 g (0.022 mol) of 4-methylphenylboronic acid, 4.66 g (0.044 mol) of sodium carbonate were placed in 60 ml of ethylene glycol/12 ml of water in the reaction vessel, the mixture was degassed a number of times and saturated with argon. After addition of 22.4 mg (0.1 mmol) of palladium acetate and 0.114 g (0.2 mmol) of TMSPP, the reaction mixture was stirred for 2 hours at 125° C. After addition of 60 ml of water, the aqueous phase was extracted 4 times with 50 ml each time of ether, the combined ether phases were washed with 50 ml of water and 50 ml of saturated sodium chloride solution and dried over magnesium sulfate. Removal of the solvent gave 4.5 g of (21) as solid.

Workup

customsimilar to Example 16 d
customthe mixture was degassed a number of times
extractionthe aqueous phase was extracted 4 times with 50 ml each time of ether
washthe combined ether phases were washed with 50 ml of water and 50 ml of saturated sodium chloride solution
dry with materialdried over magnesium sulfate
customRemoval of the solvent

Sources & evidence

ORD record: ord-abbf714f7e734e84ad4d23cfe5e72f0b
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06963017B2

Reaction notes

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