Cesium carbonate → 4-(4-(Trifluoromethyl)phenoxy)benzaldehyde

HRID 705882Notes

Reaction equation

HRID 705882 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.F[C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:4]=[CH:5][C:6]([O:9][C:13]2[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 678744-(Trifluoromethyl)phenolHCID 680234-Fluorobenzaldehyde

Product 1

HCID 133008444-(4-(Trifluoromethyl)phenoxy)benzaldehydeYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 4-(trifluoromethyl)phenol (3 g, 18.51 mmol) and 4-fluorobenzaldehyde (2.3 g, 18.53 mmol) in DMF (20 mL), was added Cs2CO3 (7.24 g, 22.21 mmol). The mixture was heated with a microwave condition at 120° C. for 4 h. After cooling, the reaction mixture was diluted in water, extracted with EA. The organic phase was washed with water and brine, dried over Na2SO4 and evaporated in vacuo to afford the title compound (4.68 g, 95% yield) as a brown oil. LCMS: rt=3.58 min, [M+H+]=267

Workup

  1. temperatureAfter cooling
  2. extractionextracted with EA
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-df5ad8f9bce94d449f36e95079f668b6
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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