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

HRID 1842986Notes

Reaction equation

HRID 1842986 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[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:9]=[CH:8][C:5]([CH2:6][NH:7][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-fluorobenzylamine (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 (EtOAc). Drying (MgSO4) and evaporation of the ethyl acetate followed and the residue was purified by CC (eluent EtOAc/n-hexane) to yield 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 (EtOAc)
  3. customDrying
  4. custom(MgSO4) and evaporation of the ethyl acetate
  5. customthe residue was purified by CC (eluent EtOAc/n-hexane)

Sources & evidence

ORD record
ord-ca39859f1b1f47f09ed664ed68c9e331
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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