Cesium carbonate → 4-(4'-Methoxybiphenyl-3-yloxy)-benzaldehyde

HRID 2217637Notes

Reaction equation

HRID 2217637 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[CH:10]=2)=[CH:5][CH:4]=1.F[C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:17]3[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][CH:18]=3)[CH:10]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 680234-FluorobenzaldehydeHCID 102858703-(4-Methoxyphenyl)phenol

Product 1

HCID 593029604-(4'-Methoxybiphenyl-3-yloxy)-benzaldehydeYield 67.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 56 (1.20 g, 6.0 mmol) and 4-fluorobenzaldehyde (745 mg, 6.0 mmol) in DMF (25 mL) was added cesium carbonate (3.90 g, 12.0 mmol). After stirring for 1 h at 100° C., the product was partitioned between ethyl acetate (100 mL) and water (100 mL). The organic layer was washed with water (100 mL), brine (100 mL), dried (MgSO4), filtered and concentrated in vacuo. The crude product was dissolved in dichloromethane and adsorbed onto silica gel and purified by flash chromatography using hexanes-ethyl acetate (6:1) to yield 57 (1.23 g, 67%) as a white solid after solvent removal.

Workup

  1. customthe product was partitioned between ethyl acetate (100 mL) and water (100 mL)
  2. washThe organic layer was washed with water (100 mL), brine (100 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. dissolutionThe crude product was dissolved in dichloromethane
  7. custompurified by flash chromatography

Sources & evidence

ORD record
ord-7c5a33ebe3e0449e98dbf3b346a07cb5
Source dataset
uspto-grants-2008_08
Patent number
US07407978B2

Reaction notes

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