Potassium Carbonate → 4-(4-bromo-3,5-dimethylphenyl)-3,6-dihydro-2H-pyran

HRID 1043930Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].FC(F)(F)S(O[C:13]1[CH:18]=[C:17]([CH3:19])[C:16]([Br:20])=[C:15]([CH3:21])[CH:14]=1)(=O)=O.[O:24]1[CH2:29][CH:28]=[C:27](B2OC(C)(C)C(C)(C)O2)[CH2:26][CH2:25]1>CN(C=O)C>[Br:20][C:16]1[C:17]([CH3:19])=[CH:18][C:13]([C:27]2[CH2:28][CH2:29][O:24][CH2:25][CH:26]=2)=[CH:14][C:15]=1[CH3:21]

Participants

Conditions

Temperature: 85 °C

Procedure

Potassium carbonate (1.99 g) and Pd(dppf)Cl2-DCM complex (196 mg) were added to a solution of 4-bromo-3,5-dimethylphenyl trifluoromethanesulfonate (1.6 g) and 3,6-dihydro-2H-pyran-4-boronic acid pinacol ester (CAS No. 287944-16-5) (1.11 g) in DMF (16 mL). The reaction mixture was stirred at 85° C. for four hours. The reaction mixture was returned to room temperature, and the reaction mixture was then concentrated under reduced pressure. MTBE, water and brine were added to the residue, and the organic layer was separated. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 2%) to give the title compound (747 mg).

Workup

customwas returned to room temperature
concentrationthe reaction mixture was then concentrated under reduced pressure
additionMTBE, water and brine were added to the residue
customthe organic layer was separated
washThe organic layer was washed with brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 2%)

Sources & evidence

ORD record: ord-3031b90b51404e7285f9ff18a5bf238c
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563565B2

Reaction notes

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