(Diethylamino)sulfur trifluoride → 2-chloro-4-fluoro-5-[4-(fluoromethyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]benzoic acid, 1-methylethyl ester

HRID 1488750Notes

Reaction equation

HRID 1488750 reaction equation
[Cl:1][C:2]1[CH:13]=[C:12]([F:14])[C:11]([C:15]2[C:19]([CH2:20]O)=[C:18]([C:22]([F:25])([F:24])[F:23])[N:17]([CH3:26])[N:16]=2)=[CH:10][C:3]=1[C:4]([O:6][CH:7]([CH3:9])[CH3:8])=[O:5].C(N(S(F)(F)[F:33])CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:13]=[C:12]([F:14])[C:11]([C:15]2[C:19]([CH2:20][F:33])=[C:18]([C:22]([F:24])([F:25])[F:23])[N:17]([CH3:26])[N:16]=2)=[CH:10][C:3]=1[C:4]([O:6][CH:7]([CH3:8])[CH3:9])=[O:5]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 571742762-chloro-4-fluoro-5-[4-(hydroxymethyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]benzoic acid, 1-methylethyl ester

Product 1

HCID 571146272-chloro-4-fluoro-5-[4-(fluoromethyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]benzoic acid, 1-methylethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.5 g 2-chloro-4-fluoro-5-[4-(hydroxymethyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]benzoic acid, 1-methylethyl ester in 50ml methylene chloride was added 5 mL of diethyl aminosulfurtrifluoride and the solution stirred overnight at room temperature. The reaction mixture was poured onto ice water and the organic layer washed with brine, dried over anhydrous magnesium sulfate, filtered and the concd in vacuo to give 2-chloro-4-fluoro-5-[4-(fluoromethyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]benzoic acid, 1-methylethyl ester as a tan solid: mp 74° C.; 1HNMR (CDCl3) δ8.02 (d, 1H, J=8.0), 7.30 (d, 1H, J=9.6), 5.29 (d, 2H, J=48.0), 5.26 (m, 1H, J=6.0), 4.09 (s, 3H), 1.37 (d, 6H, J=6.4).

Workup

  1. additionThe reaction mixture was poured onto ice water
  2. washthe organic layer washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered

Sources & evidence

ORD record
ord-e52ebf7649564e0e94359f45e099650e
Source dataset
uspto-grants-1997_10
Patent number
US05675017

Reaction notes

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