Boron tribromide → N-(3-bromo-propyl)-3-hydroxy-benzenesulfonamide

HRID 1060895Notes

Reaction equation

HRID 1060895 reaction equation
O[CH2:2][CH2:3][CH2:4][NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15]C)[CH:10]=1)(=[O:8])=[O:7].B(Br)(Br)[Br:18]>C(Cl)Cl>[Br:18][CH2:2][CH2:3][CH2:4][NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[CH:10]=1)(=[O:8])=[O:7]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 18629442N-(3-hydroxy-propyl)-3-methoxy-benzenesulfonamide

Product 1

HCID 18629458N-(3-bromo-propyl)-3-hydroxy-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-(3-Hydroxy-propyl)-3-methoxy-benzenesulfonamide (0.478 g, 1.95 mmol) in CH2Cl2(10 mL) at 0° C. was treated with BBr3 (9.74 mL of a 1M solution in CH2Cl2, 9.74 mmol) then left to warm to room temperature. After 1 h, the reaction mixture was concentrated in vacuo, neutralized to pH 6 with aqueous saturated NaHCO3 solution, and extracted with CH2Cl2 (3×20 mL), dried (MgSO4), filtered and concentrated to give the title compound. MS (M+1) 294.

Workup

  1. waitthen left
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. extractionextracted with CH2Cl2 (3×20 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-61e8af625435428992fdbbe3d60a63c4
Source dataset
uspto-grants-2003_02
Patent number
US06525074B2

Reaction notes

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