Potassium Carbonate → 5-(2-methylphenyl)furan-2-carbaldehyde
Reaction equation
Br[C:2]1[O:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1B(O)O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:2]1[O:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 25 °C
Procedure
As illustrated in Scheme 1, to a mixture of 5-bromo-2-furaldehyde (2.0 g, 11.4 mmol), tetrabutylammonium bromide (3.7 g, 11.4 mmol), potassium carbonate (3.93 g, 28.5 mmol), 2-methylphenyl boronic acid (1.7 g, 12.5 mmol) and palladium (II) acetate (55.2 mg, 0.23 mmol) is added water (20 mL). The reaction mixture is then stirred vigorously for 16 hour at 25° C. Once complete, the reaction mixture is poured into a separatory funnel and diluted with water (50 mL) and ethyl acetate (150 mL). The organic layer is separated and treated with 5.0 g of activated charcoal for 30 min after which time the suspension is filtered through a pad of celite and the filtrate concentrated to afford the crude coupling product as a yellow oil. The crude product is purified by column chromatography (5→10% ethyl acetate in hexanes) to afford 1.8 g of 5-(2′-methylphenyl)-2-furaldehyde.
Workup
- additionOnce complete, the reaction mixture is poured into a separatory funnel
- customThe organic layer is separated
- additiontreated with 5.0 g of activated charcoal for 30 min after which time the suspension
- filtrationis filtered through a pad of celite
- concentrationthe filtrate concentrated
- customto afford the crude coupling product as a yellow oil
- customThe crude product is purified by column chromatography (5→10% ethyl acetate in hexanes)
Sources & evidence
- ORD record
- ord-47a93ed042064c049795a29034a68b77
- Source dataset
- uspto-grants-2006_05
- Patent number
- US07041690B2
Reaction notes
Loading…