p-Toluenesulfonic acid → HCID 53671963, compound

HRID 342987Notes

Reaction equation

HRID 342987 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-2d70d05f380a4d34a22ce7993540d1cc
Source dataset
uspto-grants-1999_01
Patent number
US05859283

Reaction notes

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