p-Toluenesulfonic acid → HCID 53671963, compound

HRID 266545Notes

Reaction equation

HRID 266545 reaction equation
[Br:1][C:2]1[C:22]([O:23][CH2:24][CH2:25][O:26][CH3:27])=[C:21]([S:28]([CH3:31])(=[O:30])=[O:29])[CH:20]=[CH:19][C:3]=1[C:4]([CH:6]([C:14]([CH:16]1[CH2:18][CH2:17]1)=[O:15])C(OC(C)(C)C)=O)=[O:5].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH:16]1([C:14](=[O:15])[CH2:6][C:4]([C:3]2[CH:19]=[CH:20][C:21]([S:28]([CH3:31])(=[O:30])=[O:29])=[C:22]([O:23][CH2:24][CH2:25][O:26][CH3:27])[C:2]=2[Br:1])=[O:5])[CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 67601198HCID 67601198, compound

Product 1

HCID 53671963HCID 53671963, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of crude t-butyl 2-[2-bromo-3-(2-methoxyethoxy)-4-methylsulphonylbenzoyl]-3-cyclopropyl-3-oxopropanoate (10.2 g) and 4-toluenesulphonic acid (2 g) in dry toluene was stirred and heated at reflux for 2 hours. The cooled mixture was washed with water, dried (anhydrous magnesium sulphate) and filtered. The filtrate was evaporated to dryness to give 3-cyclopropyl-1-[2-bromo-3-(2-methoxyethoxy)-4-methylsulphonylphenyl]propan-1,3-dione (7.5 g) as a brown oil which was not purified further NMR(CDCl3) 0.9(4H, m), 1.5(1H, m), 3.1(3H, s), 3.3(3H,s), 3.6(2H, t), 4.2(2H, t), 5.7(1H, s), 7.15(1H, d), 7.8(1H, d).

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. washThe cooled 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-9c89427af3d24ecba832d3a6c9ff6e4c
Source dataset
uspto-grants-1997_07
Patent number
US05650533

Reaction notes

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