Potassium peroxymonosulphate → 4-[(4-Fluorophenyl)ethynyl]benzoic acid

HRID 551940Notes

Reaction equation

HRID 551940 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.S([O-])(O[O-])(=O)=[O:19].[K+].[K+]>CN(C=O)C.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]#[C:9][C:10]2[CH:11]=[CH:12][C:13]([C:14]([OH:19])=[O:15])=[CH:16][CH:17]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 10313463Potassium peroxymonosulphateHCID 454901144-[2-(4-Fluorophenyl)ethynyl]benzaldehyde

Product 1

HCID 226288574-[(4-Fluorophenyl)ethynyl]benzoic acidYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[(4-fluorophenyl)ethynyl]benzaldehyde (10.39 g; 46.37 mmol, intermediate which may be obtained according to methods disclosed in EP03 103780.7) in DMF (400 mL) was added potassium peroxomonosulfate (28.5 g, 46.4 mmol) in one portion at rt. The reaction mixture was stirred at rt overnight. The reaction mixture was poured in water (2 L) and the resulting precipitate was filtered off, washed with water and dried under reduced pressure to give 10.45 g (94%) of the title compound as a white powder. HPLC, Rt: 3.98 min (purity: 98.6%). 1H NMR (DMSO-d6) δ: 13.15 (brs, 1H), 7.96 (d, J=8.1 Hz, 2H), 7.64 (m, 4H), 7.29 (t, J=8.9 Hz, 2H).

Workup

  1. filtrationthe resulting precipitate was filtered off
  2. washwashed with water
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-45dc4f89ac30406f97bc289cace16dce
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

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