Potassium Carbonate → 4'-Chlorobiphenyl-2-carbaldehyde

HRID 1919543Notes

Reaction equation

HRID 1919543 reaction equation
Br[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[Cl:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC(C)=O.O>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:2]2[C:3]([CH:4]=[O:5])=[CH:6][CH:7]=[CH:8][CH:9]=2)=[CH:13][CH:12]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 811292-Bromobenzaldehyde

Product 1

HCID 13936894'-Chlorobiphenyl-2-carbaldehydeYield 76%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 167845palladium(II) acetateCatalystHCID 18366337Propan-2-one--water (1/1)Solvent

Conditions

Temperature
40 °C

Procedure

2-Bromobenzaldehyde a (19 mmol), 4-chlorophenyl boronic acid b (19 mmol), tetrabutylammonium iodide (0.19 mmol), potassium carbonate (57 mmol) and palladium acetate (0.12 mmol) in mixture of acetone/water (25 ml/25 ml) was stirred at 40° C. for 30 mins. The mixture was partitioned between ethyl acetate and water and the layers were separated. The organic layer was dried (MgSO4) and concentrated in vacuo. The resulting residue was applied to silica chromatography gradient eluting with 100% petroleum ether to 5% ethyl acetate/petroleum ether to yield intermediate c 4′-chloro-biphenyl-2-carbaldehyde as a colourless oil (76%). 1H NMR (300 MHz, CDCl3) δ 9.96 (1H, s), 8.02 (1H, dd, J 7.8 and 1.0 Hz), 7.64-7.30 (7H, m, ArH).

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. customthe layers were separated
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. washeluting with 100% petroleum ether to 5% ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-46d3173c470549a0b55e4e41f44be0cf
Source dataset
uspto-grants-2012_05
Patent number
US08168645B2

Reaction notes

Loading…