Bromine → N-(5-(2-bromoacetyl)-2-hydroxyphenyl)methanesulfonamide

HRID 1955786Notes

Reaction equation

HRID 1955786 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[NH:11][S:12]([CH3:15])(=[O:14])=[O:13].[Br:16]Br>O1CCOCC1>[Br:16][CH2:9][C:8]([C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[C:3]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:4]=1)=[O:10]

Participants

4

Reactant 2

HCID 24408BromineHCID 19073226N-(5-acetyl-2-hydroxyphenyl)methanesulfonamide

Product 1

HCID 19073169N-(5-(2-bromoacetyl)-2-hydroxyphenyl)methanesulfonamideYield 90.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred 60° C. dioxane (35 mL) solution of 1-[4-hydroxy-3-[(methylsulfonyl)amino]phenyl]ethanone (2.06 g, 8.7 mmol) was rapidly added Br2 (1.48 g, 9.2 mmol). After one hour, the solution was cooled, concentrated and diluted with H2O. After filtration, the product was washed thoroughly with H2O, then with i-PrOH (9 mL), and air-dried to obtain the title compound (2.43 g, 84%).

Workup

  1. customTo a stirred 60° C.
  2. temperaturethe solution was cooled
  3. concentrationconcentrated
  4. additiondiluted with H2O
  5. filtrationAfter filtration
  6. washthe product was washed thoroughly with H2O
  7. dry with materialwith i-PrOH (9 mL), and air-dried

Sources & evidence

ORD record
ord-b3ea20147bd9433e8acbac29c47f0f5f
Source dataset
uspto-grants-1998_07
Patent number
US05776983

Reaction notes

Loading…