Methanol → 2-Hydroxybenzene-1-sulfonamide

HRID 1249288Notes

Reaction equation

HRID 1249288 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.

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-2d8367af5ec94886aec9c9a46121b62e
Source dataset
uspto-grants-1986_12
Patent number
US04629810

Reaction notes

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