3-(Trifluoromethyl)phenol → 4-(3-(Trifluoromethyl)phenoxy)benzaldehyde

HRID 705826Notes

Reaction equation

HRID 705826 reaction equation
C([O-])([O-])=O.[K+].[K+].[F:7][C:8]([F:17])([F:16])[C:9]1[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=1.F[C:19]1[CH:26]=[CH:25][C:22]([CH:23]=[O:24])=[CH:21][CH:20]=1>CN(C=O)C>[F:7][C:8]([F:16])([F:17])[C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=1)[O:15][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=[O:24])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 73763-(Trifluoromethyl)phenolHCID 11430Potassium CarbonateHCID 680234-Fluorobenzaldehyde

Product 1

HCID 121487884-(3-(Trifluoromethyl)phenoxy)benzaldehydeYield 85.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

K2CO3 (23.45 g, 170 mmol) was added to a solution of 3-(trifluoromethyl)phenol (25 g, 154 mmol) and 4-fluorobenzaldehyde (19.14 g, 154 mmol) in DMF (300 mL), and the reaction mixture was stirred at 140° C. for 4 h. After cooling down to room temperature, the reaction mixture was poured into ice water (2500 ml), extracted with ethyl acetate (500 ml×2), and washed with brine (200 mL×2). The organic phase was dried with sodium sulfate, filtered, and concentrated to give the title compound as a brown solid (35 g, 66.9% yield). LCMS: rt=1.62 min, [M+H+]=267

Workup

  1. temperatureAfter cooling down to room temperature
  2. extractionextracted with ethyl acetate (500 ml×2)
  3. washwashed with brine (200 mL×2)
  4. dry with materialThe organic phase was dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f999403ed8454d53b96daa2e83341ed1
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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