Potassium Carbonate → 4-Bromo-3-methyl-2-methylsulfonylaniline

HRID 460503Notes

Reaction equation

HRID 460503 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][C:8]1[C:9]([S:15]([CH3:18])(=[O:17])=[O:16])=[C:10]([CH:12]=[CH:13][CH:14]=1)[NH2:11].[Br-:19].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>C(#N)C>[Br:19][C:14]1[CH:13]=[CH:12][C:10]([NH2:11])=[C:9]([S:15]([CH3:18])(=[O:17])=[O:16])[C:8]=1[CH3:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18446118497227-21-1HCID 23500184Tetra-n-butylammonium tribromide

Product 1

HCID 184461204-Bromo-3-methyl-2-methylsulfonylanilineYield 82.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

400 g (2.9 mol) of potassium carbonate were added to a solution of 134 g (0.73 mol) of 3-methyl-2-methylsulfonylaniline in 1200 ml of acetonitrile. At room temperature, 320 g (0.65 mol) of tetrabutylammonium tribromide were then added a little at a time, with vigorous stirring. The resulting precipitate was separated off, methyl tert-butyl ether was added to the filtrate and the filtrate was extracted with dilute hydrochloric acid and then with water. The organic phase was concentrated to dryness under reduced pressure. The resulting residue was once more taken up in methyl tert-butyl ether and washed two more times with hydrochloric acid and water. The organic phase was dried and concentrated under reduced pressure, giving 142 g (74%) of 4-bromo-3-methyl-2-methylsulfonylaniline as a brown solid of melting point 103–106° C.

Workup

  1. customThe resulting precipitate was separated off
  2. additionmethyl tert-butyl ether was added to the filtrate
  3. extractionthe filtrate was extracted with dilute hydrochloric acid
  4. concentrationThe organic phase was concentrated to dryness under reduced pressure
  5. washwashed two more times with hydrochloric acid and water
  6. customThe organic phase was dried
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d0732dec0e2d48b6b44739e4dfdaecec
Source dataset
uspto-grants-2007_03
Patent number
US07196229B2

Reaction notes

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