Ethanesulfonyl chloride → N-(4-bromo-2-fluorobenzyl)ethanesulfonamide

HRID 1428769Notes

Reaction equation

HRID 1428769 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH2:9])=[C:4]([F:10])[CH:3]=1.[CH2:11]([S:13](Cl)(=[O:15])=[O:14])[CH3:12]>N1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][S:13]([CH2:11][CH3:12])(=[O:15])=[O:14])=[C:4]([F:10])[CH:3]=1

Participants

4

Reactant 2

HCID 11667Ethanesulfonyl chlorideHCID 3770848(4-Bromo-2-fluorophenyl)methanamine

Product 1

HCID 70816043N-(4-bromo-2-fluorobenzyl)ethanesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

(4-Bromo-2-fluorophenyl)methanamine (924 mg, 4.53 mmol) was dissolved in pyridine and ethane sulfonyl chloride (0.82 mL, 8.60 mmol) was added to the solution at 0° C. The mixture was stirred for 1 h at 0° C. Then, the mixture was quenched with 1N HCl and extracted with ethyl acetate. Drying over magnesium sulfate and evaporation of the ethyl acetate and purified by column chromatography gave N-(4-bromo-2-fluorobenzyl)-ethanesulfonamide in pure form (1.06 g, 79%).

Workup

  1. customThen, the mixture was quenched with 1N HCl
  2. extractionextracted with ethyl acetate
  3. dry with materialDrying over magnesium sulfate and evaporation of the ethyl acetate
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-4ad33e7a18a64304ac8b533d122f3afb
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

Loading…