Chlorosulfonic acid → 4-{[4-(Trifluoromethyl)pyrimidin-2-yl]oxy}benzene-1-sulfonyl chloride

HRID 2070120Notes

Reaction equation

HRID 2070120 reaction equation
[O:1]([C:8]1[N:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:18][S:19](O)(=[O:21])=[O:20]>ClC(Cl)C.C(Cl)Cl>[F:15][C:14]([F:17])([F:16])[C:12]1[CH:11]=[CH:10][N:9]=[C:8]([O:1][C:2]2[CH:3]=[CH:4][C:5]([S:19]([Cl:18])(=[O:21])=[O:20])=[CH:6][CH:7]=2)[N:13]=1

Participants

5

Reactant 2

HCID 24638Chlorosulfonic acidHCID 538928452-Phenoxy-4-(trifluoromethyl)pyrimidine

Product 1

HCID 455943214-{[4-(Trifluoromethyl)pyrimidin-2-yl]oxy}benzene-1-sulfonyl chloride

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-phenoxy-4-trifluoromethylpyrimidine (3.0 g, 12.5 mmol, prepared under a) in dichloroethane (30 ml) was added a solution chlorosulfonic acid (10.2 g, 88 mmol) in DCM (20 ml). The reaction mixture was stirred 7 h at 50° C. Subsequently the reaction mixture was slowly quenched with water and extracted with MTBE. The organic layer was washed with water and dried and the solvent was removed in vacuo. The residue was suspended in n-pentane and stirred for 10 minutes. Filtration yielded 4-(4-trifluoromethylpyrimidin-2-oxy)benzenesulfonyl chloride as a brownish solid (1.5 g). 1H-NMR (CDCl3): δ=7.5 (m, 3H), 8.17 (m, 2H), 8.9 ppm (m, 1H).

Workup

  1. customSubsequently the reaction mixture was slowly quenched with water
  2. extractionextracted with MTBE
  3. washThe organic layer was washed with water
  4. customdried
  5. customthe solvent was removed in vacuo
  6. stirringstirred for 10 minutes
  7. filtrationFiltration

Sources & evidence

ORD record
ord-72b57045681543a88fd1860784035c9f
Source dataset
uspto-grants-2012_10
Patent number
US08299262B2

Reaction notes

Loading…