Potassium Carbonate → 4-(4-(Trifluoromethyl)phenoxy)benzaldehyde

HRID 1777004Notes

Reaction equation

HRID 1777004 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-].[K+].[K+]>CN(C)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

5

Reactant 3

HCID 11430Potassium CarbonateHCID 678744-(Trifluoromethyl)phenolHCID 680234-Fluorobenzaldehyde

Product 1

HCID 133008444-(4-(Trifluoromethyl)phenoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-(trifluoromethyl)phenol (4.86 g, 1 equiv), 4-fluorobenzaldehyde (3.22 mL, 1 equiv), potassium carbonate (4.15 g, 1 equiv) and dimethylformamide (60 mL) was stirred at 150° C. under argon for 3 hours, then poured into ice/water. The precipitate was filtered off, washed with water, then extracted with hot ethanol. Undissolved solid was removed by filtration, and the filtrate evaporated and purified by chromatography on silica. 1H-NMR (CDCl3) δ 7.14 (4H,m), 7.66 (2H,m), 7.90 (2H,m), 9.97 (1H,s); MS (APCI+) found (M+1)=267; C14H9F3O2 requires 266.

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with water
  3. extractionextracted with hot ethanol
  4. customwas removed by filtration
  5. customthe filtrate evaporated
  6. custompurified by chromatography on silica

Sources & evidence

ORD record
ord-33cefba5177347c3813a822c334c117c
Source dataset
uspto-grants-2016_02
Patent number
US09266841B2

Reaction notes

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