Trifluoroacetic acid → 5-(4-Fluorophenyl)-1-methyl-1H-pyrazole-3-carboxaldehyde

HRID 271298Notes

Reaction equation

HRID 271298 reaction equation
C[O:2][CH:3](OC)[C:4]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[N:6]([CH3:16])[N:5]=1.FC(F)(F)C(O)=O>O>[F:15][C:12]1[CH:11]=[CH:10][C:9]([C:7]2[N:6]([CH3:16])[N:5]=[C:4]([CH:3]=[O:2])[CH:8]=2)=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 586948315-(4-fluorophenyl)-1-methyl-1H-pyrazol-3-carboxaldehyde dimethyl acetal

Product 1

HCID 288086345-(4-Fluorophenyl)-1-methyl-1H-pyrazole-3-carboxaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The compound from Step 1 (9 g) was treated with trifluoroacetic acid (30 mL) and water (30 mL). The trifluoacetic acid was removed in vacuo and the reaction mixture partitioned between ethyl acetate and saturated sodium bicarbonate. The organic layer was washed with saturated sodium bicarbonate (×2), brine and dried over MgSO4. The solvent was removed in vacuo to give a yellow oil which was crystallised from ethyl acetate/hexanes to give the title compound. 4.6 g 1H NMR (360, CDCl3) δ 9.97 (s, 1H), 7.38 (m, 2H), 7.20 (m, 2H), 6.80 (s, 1H), 3.95 (s, 3H).

Workup

  1. customThe trifluoacetic acid was removed in vacuo
  2. customthe reaction mixture partitioned between ethyl acetate and saturated sodium bicarbonate
  3. washThe organic layer was washed with saturated sodium bicarbonate (×2), brine
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed in vacuo
  6. customto give a yellow oil which
  7. customwas crystallised from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-787cd75cd0f34556a74a0182bef58d23
Source dataset
uspto-grants-2008_11
Patent number
US07452899B2

Reaction notes

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