Methanesulfonyl chloride → N-(3-Bromo-5-(trifluoromethyl)phenyl)methanesulfonamide

HRID 733186Notes

Reaction equation

HRID 733186 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:5]=[C:6]([Br:8])[CH:7]=1.[CH3:13][S:14](Cl)(=[O:16])=[O:15]>N1C=CC=CC=1.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[Br:8][C:6]1[CH:7]=[C:2]([NH:1][S:14]([CH3:13])(=[O:16])=[O:15])[CH:3]=[C:4]([C:9]([F:12])([F:10])[F:11])[CH:5]=1

Participants

6

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 27358803-Bromo-5-(trifluoromethyl)aniline

Product 1

HCID 65491442N-(3-Bromo-5-(trifluoromethyl)phenyl)methanesulfonamideYield 99.6%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-Amino-5-bromobenzotrifluoride (200 mg) in pyridine (2 mL) was added methane sulphonyl chloride (115 mg) and one crystal of 4-(dimethyl-amino)pyridine. The mixture was stirred at room temperature for four hours then diluted with ethyl acetate (50 mL) and washed with HCl (2M, 50 mL) and saturated sodium chloride solution (50 mL). Organics were separated, dried over sodium sulphate, filtered, and solvent was removed under reduced pressure to yield N-(3-bromo-5-trifluoromethyl-phenyl)-methanesulfonamide (264 mg).

Workup

  1. washwashed with HCl (2M, 50 mL) and saturated sodium chloride solution (50 mL)
  2. customOrganics were separated
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customsolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-2a24ce1fa7204efb8ea985aec472f037
Source dataset
uspto-grants-2009_09
Patent number
US07589095B2

Reaction notes

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