4-Aminophenyl trifluoromethyl sulphone → HCID 67236489, compound

HRID 1471010Notes

Reaction equation

HRID 1471010 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][CH2:10][C:11]([C:13]2[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=2)=O)=[CH:4][CH:3]=1.[F:21][C:22]([F:34])([F:33])[S:23]([C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=1)(=[O:25])=[O:24]>C1(C)C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:30]([C:29]3[CH:31]=[CH:32][C:26]([S:23]([C:22]([F:34])([F:21])[F:33])(=[O:25])=[O:24])=[CH:27][CH:28]=3)[C:11]([C:13]3[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 1363154-Aminophenyl trifluoromethyl sulphoneHCID 2192171,4-Bis(4-bromophenyl)-1,4-butanedione

Product 1

HCID 67236489HCID 67236489, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 1140TolueneSolvent2×

Procedure

To a slurry of the product from Example 26E (0.60 g, 1.52 mmol) and 4-(trifluoromethylsulfonyl)aniline (0.51 g, 2.27 mmol) in toluene (12 mL) was added a 1N solution of titanium(IV) chloride (1.6 mL, 1.6 mmol) in toluene. The mixture was stirred overnight at room temperature and then heated to reflux for 3 hours. The cooled mixture was filtered and the solid residue was suspended in a mixture of water and diethyl ether. The solid was diluted with water and ether and stirred vigorously for 15 minutes. The mixture was filtered and then washed thoroughly with diethyl ether to give the title compound as a crude mixture that was used in subsequent reactions without further purification (0.60 g, 68% yield crude).

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 hours
  3. filtrationThe cooled mixture was filtered
  4. additionthe solid residue was suspended in a mixture of water and diethyl ether
  5. additionThe solid was diluted with water and ether
  6. stirringstirred vigorously for 15 minutes
  7. filtrationThe mixture was filtered
  8. washwashed thoroughly with diethyl ether

Sources & evidence

ORD record
ord-53cc263a7f814180ba238897694a0412
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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