Sodium Carbonate → 2'-TrifluoroMethyl-Biphenyl-4-Carbaldehyde
Reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)=[O:2].C([O-])([O-])=O.[Na+].[Na+].O1CCOCC1.I[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:31]([F:34])([F:33])[F:32]>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:32][C:31]([F:34])([F:33])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[C:6]1[CH:7]=[CH:8][C:3]([CH:1]=[O:2])=[CH:4][CH:5]=1Participants
Procedure
To a solution of 4-formylbenzeneboronic acid (4.00 g, 26.7 mmol) and Na2CO3 (5.66 g, 53.4 mmol) in water (240 mL) was added p-dioxane (240 mL). This mixture was treated sequentially with 2-iodobenzotrifluoride (3.74 mL, 26.7 mmol) and palladium (II) acetate (540 mg, 2.40 mmol) and allowed to stir at ambient temperature for 24 hours. The solvent was evaporated in vacuo. To the residue was added EtOAc (400 inL) and water (300 mL). The aqueous layer was acidified to pH 2 with 1.0 N aq. HCl and the layers separated. The aqueous layer was extracted with EtOAc (2×200 mL). The organic extracts were combined, washed with brine (200 mL), 5% aq. Na2S2O3 (200 mL), saturated NaCl (200 mL), dried (Na2SO4), and the solvent evaporated in vacuo and the residue chromatographed (Silica gel, 20-50% CH2Cl2 in hexanes) to afford the title compound.
Workup
- customThe solvent was evaporated in vacuo
- additionTo the residue was added EtOAc (400 inL) and water (300 mL)
- customthe layers separated
- extractionThe aqueous layer was extracted with EtOAc (2×200 mL)
- washwashed with brine (200 mL), 5% aq. Na2S2O3 (200 mL), saturated NaCl (200 mL)
- dry with materialdried (Na2SO4)
- customthe solvent evaporated in vacuo
- customthe residue chromatographed (Silica gel, 20-50% CH2Cl2 in hexanes)
Sources & evidence
- ORD record
- ord-162929c10a6449a3b61c7246114d6f79
- Source dataset
- uspto-grants-2000_06
- Patent number
- US06080870
Reaction notes
Loading…