Potassium Carbonate → HCID 68481774, compound

HRID 523508Notes

Reaction equation

HRID 523508 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]([CH3:14])=[CH2:13])=[C:6](I)[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]2[O:10][CH2:11][C:12]([CH2:14][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)([CH3:13])[C:6]=2[CH:5]=1)=[O:16]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 53243417HCID 53243417, compound

Product 1

HCID 68481774HCID 68481774, compoundYield 52.2%

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
115 °C

Procedure

To a solution of 3-Iodo-4-(2-methyl-allyloxy)-benzoic acid methyl ester (455 mg, 1.37 mmol) in DMF (15 mL) were added Potassium carbonate (379 mg, 2.74 mmol), Tetrabutylammonium chloride (380 mg, 1.37 mmol), a solution of Palladium acetate (25.6 mg, 0.136 mmol) in DMF (5 mL) and Phenylboronic acid (200 mg, 1.64 mmol). The resulting mixture was stirred for 3 h at 115° C., cooled to room temperature, filtered over silica, washed with water, dryed over MgSO4 and concentrated. Column chromatography (silica gel, heptane/CH2Cl2: 4/6) afforded 202 mg (52%) of the title compound as a slight brown oil.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered over silica
  3. washwashed with water
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c9bcf51e68714e9ab41e30de24c864fa
Source dataset
uspto-grants-2016_05
Patent number
US09339486B2

Reaction notes

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