Sodium Carbonate → 3-(4-Bromo-3,5-dimethylphenyl)furan
Reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5](Br)=[CH:4][C:3]=1[CH3:10].C([O-])([O-])=O.[Na+].[Na+].[O:17]1[CH2:22][CH2:21]O[CH2:19][CH2:18]1>>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:19]2[CH:21]=[CH:22][O:17][CH:18]=2)=[CH:4][C:3]=1[CH3:10]Participants
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 2,5-dibromo-1,3-dimethylbenzene (2.00 g), 1-furan-3-ylboronic acid (856 mg), and 2 M aqueous Na2CO3 solution (11 mL) in 1,4-dioxane (40 mL) is purged with argon for 5 min. Tetrakis-triphenylphosphine-palladium-(0) (270 mg) is added and the mixture is stirred at 100° C. over night. More tetrakis-triphenylphosphine-palladium-(0) (50 mg) is added and the mixture is stirred for another 5 h at 100° C. After cooling to room temperature the mixture is diluted with ethyl acetate and aqueous NH4Cl solution. The aqueous phase is extracted with ethyl acetate and the combined extracts are washed with brine, dried over MgSO4 and concentrated in vacuo. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 100:0→90:10) to give the title compound. LC (method 7): tR=1.22 min; Mass spectrum (EI+): m/z=250 [M]+.
Workup
- customis purged with argon for 5 min
- additionTetrakis-triphenylphosphine-palladium-(0) (270 mg) is added
- additionMore tetrakis-triphenylphosphine-palladium-(0) (50 mg) is added
- stirringthe mixture is stirred for another 5 h at 100° C
- temperatureAfter cooling to room temperature the mixture
- additionis diluted with ethyl acetate and aqueous NH4Cl solution
- extractionThe aqueous phase is extracted with ethyl acetate
- washthe combined extracts are washed with brine
- dry with materialdried over MgSO4
- concentrationconcentrated in vacuo
- customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 100:0→90:10)
Sources & evidence
- ORD record
- ord-f154be457bf6438aa528ccb3f64bc831
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08642585B2
Reaction notes
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