Boron tribromide → 2-[2-(4-Chloro-phenyl)-ethanesulfonylamino]-5-hydroxy-benzenesulfonamide
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][S:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][C:15]=2[S:22]([NH2:25])(=[O:24])=[O:23])(=[O:12])=[O:11])=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][S:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:15]=2[S:22]([NH2:25])(=[O:24])=[O:23])(=[O:11])=[O:12])=[CH:4][CH:3]=1Participants
4
Procedure
To a solution of 2-[2-(4-chloro-phenyl)-ethanesulfonylamino]-5-methoxy-benzenesulfonamide (4.0 g, 9.90 mmol) in DCM (250 mL) at −78° C., BBr3 (1M in DCM, 70 mL, 70 mmol) was added dropwise over 20 minutes. The reaction mixture was allowed to warm to RT and the stirring was continued overnight. The reaction mixture was then cooled to −78° C., quenched by addition of methanol (20 mL) and water (50 mL), and the product was extracted with ethyl acetate. The organic extracts were washed with water, dried over sodium sulfate and concentrated under reduced pressure. The crude product was recrystallized from methanol to the title compound (3.45 g, 92%).
Workup
- temperatureThe reaction mixture was then cooled to −78° C.
- customquenched by addition of methanol (20 mL) and water (50 mL)
- extractionthe product was extracted with ethyl acetate
- washThe organic extracts were washed with water
- dry with materialdried over sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe crude product was recrystallized from methanol to the title compound (3.45 g, 92%)
Sources & evidence
- ORD record
- ord-fcbb3ec1a5c0413cae33103add68823b
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09145380B2
Reaction notes
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