Methanol → 2-Hydroxybenzene-1-sulfonamide

HRID 1633195Notes

Reaction equation

HRID 1633195 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:13]([NH2:16])(=[O:15])=[O:14].CO>C(Cl)Cl>[OH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:13]([NH2:16])(=[O:14])=[O:15]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 47391442-Methoxybenzene-1-sulfonamide

Product 1

HCID 6375462-Hydroxybenzene-1-sulfonamideYield 69.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

22.2 ml of boron tribromide are added dropwise, under nitrogen and at room temperature, over 15 minutes to a suspension of 39 g of 2-methoxyphenylsulfonamide in 210 ml of dry methylene chloride. The reaction mixture is then stirred for 1 hour at room temperature. After the mixture has been cooled to 0° C., 200 ml of methanol are added over 15 minutes and the clear solution is concentrated. The oily residue is taken up in ethyl acetate and the solution is washed twice with water, dried over sodium sulfate, and evaporated to dryness. The residue is triturated with petroleum ether, affording 25.1 g of 2-hydroxyphenylsulfonamide with a melting point of 136°-138° C. The hydroxyphenylsulfonamides of the formula VIII listed in the following Table 1 are obtained in analogous manner:

Workup

  1. temperatureAfter the mixture has been cooled to 0° C.
  2. concentrationthe clear solution is concentrated
  3. washthe solution is washed twice with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness
  6. customThe residue is triturated with petroleum ether

Sources & evidence

ORD record
ord-0939c097250447268a8747ce162b3b31
Source dataset
uspto-grants-1984_10
Patent number
US04479821

Reaction notes

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