Bromine → N-(3-(2-bromoacetyl)-5-cyanophenyl)methanesulfonamide

HRID 251829Notes

Reaction equation

HRID 251829 reaction equation
[Br:1]Br.[C:3]([C:6]1[CH:7]=[C:8]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])[CH:9]=[C:10]([C:12]#[N:13])[CH:11]=1)(=[O:5])[CH3:4]>CCOCC>[Br:1][CH2:4][C:3]([C:6]1[CH:7]=[C:8]([NH:14][S:15]([CH3:18])(=[O:16])=[O:17])[CH:9]=[C:10]([C:12]#[N:13])[CH:11]=1)=[O:5]

Participants

4

Reactant 2

HCID 24408BromineHCID 57686801N-(3-acetyl-5-cyanophenyl)methanesulfonamide

Product 1

HCID 57686827N-(3-(2-bromoacetyl)-5-cyanophenyl)methanesulfonamideYield 85%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Al(CH3)3 (20 mmol) was added dropwise to the ice-water cooled solution of DMEDA (4.4 mmol) in dry toluene (60 mL) under nitrogen. After addition, it was continued to stir for 2 hours at room temperature. Then, methyl-3-cyano-5-(methylsulfonamido)benzoate (4 mmol) was added, and the reaction mixture was heated to reflux overnight. After cooling, it was poured into diluted hydrochloric acid, the mixture was extracted with EtOAc, the combined organic layer was washed with water and brine sequentially, dried over anhydrous Na2SO4, and concentrated to afford N-(3-acetyl-5-cyanophenyl)methanesulfonamide with a yield of 35%. Br2 (1.2 mmol) was added dropwise to the solution of N-(3-acetyl-5-cyanophenyl)methanesulfonamide (1 mmol) in Et2O (50 mL). After addition, it was continued to stir for 1.5 hours. Then the reaction mixture was washed with water and brine sequentially, dried over anhydrous Na2SO4, and concentrated to afford N-(3-(2-bromoacetyl)-5-cyanophenyl)methanesulfonamide with a yield of 85%.

Workup

  1. additionAfter addition, it
  2. washThen the reaction mixture was washed with water and brine sequentially
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c0d48d462191431388f872acdbbcc501
Source dataset
uspto-grants-2011_01
Patent number
US07868001B2

Reaction notes

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