Trifluoroacetic acid → 2-(4-Fluorophenoxy)acetaldehyde

HRID 1476741Notes

Reaction equation

HRID 1476741 reaction equation
C[O:2][CH:3](OC)[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[F:12][C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH:3]=[O:2])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59346670HCID 59346670, compound

Product 1

HCID 110518692-(4-Fluorophenoxy)acetaldehyde

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Dissolve 1-(2,2-dimethoxyethoxy)-4-fluorobenzene (1.00 g, 4.99 mmol) in chloroform (5.0 mL) and treat the mixture with trifluoroacetic acid (0.755 mL, 9.99 mmol). Stir the mixture at room temperature for two days, then heat to 65° C. and stir for 4 h. Concentrate the mixture under reduced pressure to furnish the title compound as a colorless oil in ca. 70% purity, as indicated by 1H NMR analysis (550 mg, 71% uncorrected yield). 1H NMR (400 MHz, CDCl3): δ 9.85 (t, J=0.5 Hz, 1H), 7.00 (dd, J=8.9, 8.5 Hz, 2H), 6.85 (dd, J=9.5, 4.3 Hz, 2H), 4.55 (br s, 2H).

Workup

  1. temperatureheat to 65° C.
  2. stirringstir for 4 h
  3. concentrationConcentrate the mixture under reduced pressure

Sources & evidence

ORD record
ord-2589af82d320479285015e66f2b33f07
Source dataset
uspto-grants-2016_08
Patent number
US09402838B2

Reaction notes

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