p-Toluenesulfonic acid → 3-Cyclopropyl-1-(2-fluoro-4-methylsulphonylphenyl)-propan-1,3-dione

HRID 2380196Notes

Reaction equation

HRID 2380196 reaction equation
[CH:1]1([C:4](=[O:26])[CH:5]([C:13](=[O:25])[C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][C:15]=2[F:24])C(OC(C)(C)C)=O)[CH2:3][CH2:2]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH:1]1([C:4](=[O:26])[CH2:5][C:13]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:21])=[O:22])=[CH:16][C:15]=2[F:24])=[O:25])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 19931774HCID 19931774, compound

Product 1

HCID 199317613-Cyclopropyl-1-(2-fluoro-4-methylsulphonylphenyl)-propan-1,3-dioneYield 95.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of t-butyl 3-cyclopropyl-2-(2-fluoro-4-methylsulphonylbenzoyl)-3-oxopropionate (10.5 g) and p-toluenesulphonic acid (2.0 g) in toluene was stirred and heated at reflux for 4 hours. The mixture was washed with water, dried (anhydrous magnesium sulphate) and filtered. The filtrate was evaporated to dryness to give 3-cyclopropyl-1-(2-fluoro-4-methylsulphonylphenyl)-propan-l,3-dione (7.4 g) as a red gum, NMR (CDCl3); 0.9-1.3 (m,4H), 1.8-2.1 (m, 1H), 3.1 (s,3H), 6.3 (s, 1H), 7.5-8.0 (m,3H).

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 hours
  3. washThe mixture was washed with water
  4. dry with materialdried (anhydrous magnesium sulphate)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-33a0f84d9ea54d67b196b68b533a9596
Source dataset
uspto-grants-1994_11
Patent number
US05366957

Reaction notes

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