Boron tribromide → N-(5-Bromo-2-chloropyridin-3-yl)-4-hydroxybenzenesulfonamide

HRID 1052474Notes

Reaction equation

HRID 1052474 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:9][S:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=2)(=[O:12])=[O:11])[C:5]([Cl:8])=[N:6][CH:7]=1.B(Br)(Br)Br>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([NH:9][S:10]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)(=[O:12])=[O:11])[C:5]([Cl:8])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 51355175HCID 51355175, compound

Product 1

HCID 90102863N-(5-Bromo-2-chloropyridin-3-yl)-4-hydroxybenzenesulfonamideYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(5-Bromo-2-chloropyridin-3-yl)-4-methoxybenzenesulfonamide (1.49 g, 3.95 mmol) was treated with boron tribromide (1M in dichloromethane, 20 ml, 20 mmol) with dichloromethane (10 ml) as a solvent according to the method described in Example 23. The resulting crude was purified by flash chromatography using SP1® Purification System (0% to 30%, dichloromethane-ethyl acetate) to obtain 0.6 g (42% yield) of the title compound. Purity: 100%

Workup

  1. customThe resulting crude was purified by flash chromatography
  2. customSP1® Purification System (0% to 30%, dichloromethane-ethyl acetate)

Sources & evidence

ORD record
ord-d78df5e22c2c49118564629414aa8e41
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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