Boron tribromide → HCID 57750987, compound

HRID 2283307Notes

Reaction equation

HRID 2283307 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][C:14]=1[S:21]([NH2:24])(=[O:23])=[O:22])(=[O:11])=[O:10].B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:14]=1[S:21]([NH2:24])(=[O:23])=[O:22])(=[O:11])=[O:10]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68779175HCID 68779175, compound

Product 1

HCID 57750987HCID 57750987, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2,3-dichloro-benzenesulfonylamino)-5-methoxy-benzenesulfonamide (4.8 g, 11.68 mmol) in DCM (200 mL) at −20° C., BBr3 (1M in DCM, 60 mL, 60 mmol) was added dropwise over 30 minutes. The reaction mixture was allowed to warm to RT and the stirring was continued overnight. The reaction mixture was then cooled to −20° C., quenched by addition of methanol (20 mL) and volatiles were removed under reduced pressure. The residue was partitioned between water (50 mL) and ethyl acetate (100 mL). The organic phase was washed with water, dried over sodium sulfate and concentrated under reduced pressure. The crude product was recrystallized from methanol to afford the title compound (4.6 g, 65%).

Workup

  1. temperatureThe reaction mixture was then cooled to −20° C.
  2. customquenched by addition of methanol (20 mL) and volatiles
  3. customwere removed under reduced pressure
  4. customThe residue was partitioned between water (50 mL) and ethyl acetate (100 mL)
  5. washThe organic phase was washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was recrystallized from methanol

Sources & evidence

ORD record
ord-ccf7fd76ba8f4193bac5cbe9efd2e8c3
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

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