Hydrochloric Acid → 2-Hydroxy-6-iodobenzenesulfonamide

HRID 2264128Notes

Reaction equation

HRID 2264128 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8]C)[C:3]=1[S:10]([NH2:13])(=[O:12])=[O:11].B(Br)(Br)Br.Cl>ClCCl>[OH:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([I:1])[C:3]=1[S:10]([NH2:13])(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 231507892-Iodo-6-methoxybenzenesulfonamide

Product 1

HCID 231507932-Hydroxy-6-iodobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.50 g (1.60 mmol) of 2-iodo-6-methoxybenzenesulfonamide are introduced in 10 ml of dichloromethane at room temperature and this initial charge is cautiously admixed with 0.6 g (2.40 mmol) of boron tribromide. The reaction solution is stirred at room temperature for a further 45 min and then added to 2 N hydrochloric acid. Following extraction with dichloromethane, the organic phase is dried and evaporated. This gives 0.43 g (90% of theory) of 2-hydroxy-6-iodobenzenesulfonamide.

Workup

  1. additionthis initial charge
  2. extractionextraction with dichloromethane
  3. customthe organic phase is dried
  4. customevaporated

Sources & evidence

ORD record
ord-3baf6842f0b347e7b5d1e65bb7e3f475
Source dataset
uspto-grants-2010_12
Patent number
US07855166B2

Reaction notes

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