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

HRID 237564Notes

Reaction equation

[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5](Br)=[CH:4][C:3]=1[CH3:10].[O:11]1[CH2:16][CH:15]=[C:14](B2OC(C)(C)C(C)(C)O2)[CH2:13][CH2:12]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:14]2[CH2:15][CH2:16][O:11][CH2:12][CH:13]=2)=[CH:4][C:3]=1[CH3:10]

Participants

Conditions

Temperature: 60 °C

Procedure

In a microwave vial 2,5-dibromo-1,3-dimethylbenzene (800 mg), 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (640 mg) and K3PO4 (1.3 g) are suspended in toluene (12 mL) and water (1.2 mL) and purged for 10 minutes with argon. [1,1′-Bis(diphenylphosphino)-ferrocene]-dichloropalladium-(II) (100 mg) is added, the vial is sealed and the mixture is stirred at 60° C. for 12 hours. After cooling to room temperature the mixture is diluted with diethylether and washed with saturated aqueous NH4Cl solution. The organic phase is dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→60:40) to give the title compound. Yield: 404 mg.

Workup

customwater (1.2 mL) and purged for 10 minutes with argon
addition[1,1′-Bis(diphenylphosphino)-ferrocene]-dichloropalladium-(II) (100 mg) is added
customthe vial is sealed
temperatureAfter cooling to room temperature the mixture
additionis diluted with diethylether
washwashed with saturated aqueous NH4Cl solution
dry with materialThe organic phase is dried (MgSO4)
concentrationconcentrated
customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→60:40)

Sources & evidence

ORD record: ord-82ddc4e4fd2f419fa0d403445ed4b98a
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642585B2

Reaction notes

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