Hydrochloric Acid → 4-Ethyl-3-trifluoromethyl-benzenesulfonyl chloride
Reaction equation
[S:1](=[O:3])=[O:2].[CH2:4]([C:6]1[CH:11]=[CH:10][C:9](N)=[CH:8][C:7]=1[C:13]([F:16])([F:15])[F:14])[CH3:5].N([O-])=O.[Na+].[ClH:21]>C(O)(=O)C.O.[Cu]Cl>[CH2:4]([C:6]1[CH:11]=[CH:10][C:9]([S:1]([Cl:21])(=[O:3])=[O:2])=[CH:8][C:7]=1[C:13]([F:16])([F:15])[F:14])[CH3:5]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
Amounts used: 8 mL of acetic acid was saturated with sulfur dioxide, 190 mg of copper(I) chloride, 1.45 g (7.67 mmol) of 4-ethyl-3-trifluoromethyl-phenylamine dissolved in a mixture of 3 mL of acetic acid and 3 mL of concentrated hydrochloric acid, 0.635 g of sodium nitrite in 3 mL of water. Flash chromatography on silica using 0-20% ethyl acetate in hexanes afforded 0.9 g of the product as a white solid. LC-MSD spectrum not observed; HPLC retention time: 2.9 min.
Sources & evidence
- ORD record
- ord-3cf4d87f48304299a5c29dd319068b8d
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08519135B2
Reaction notes
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