Boron tribromide → HCID 22125720, compound

HRID 1858003Notes

Reaction equation

HRID 1858003 reaction equation
B(Br)(Br)Br.[F:5][C:6]1[CH:29]=[CH:28][C:9]([C:10]([C:12]2[C:21]([O:22]C)=[CH:20][CH:19]=[C:18]3[C:13]=2[CH:14]=[CH:15][C:16]([S:24]([NH2:27])(=[O:26])=[O:25])=[CH:17]3)=[O:11])=[CH:8][CH:7]=1>C(Cl)Cl.[Cl-].[Na+].O>[F:5][C:6]1[CH:29]=[CH:28][C:9]([C:10]([C:12]2[C:21]([OH:22])=[CH:20][CH:19]=[C:18]3[C:13]=2[CH:14]=[CH:15][C:16]([S:24]([NH2:27])(=[O:25])=[O:26])=[CH:17]3)=[O:11])=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 11035745HCID 11035745, compound

Product 1

HCID 22125720HCID 22125720, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Boron tribromide (55.7 ml, 1M solution in methylene chloride) was added to a suspension of 5-(4-fluorobenzoyl)-6-methoxy-2-naphthalenesulfonamide (5 g, 14 mmol), [prepared as described in example 1], in methylene chloride (100 ml) at 0° C. After 30 minutes, the reaction mixture was poured into brine and the product was extracted into methylene chloride. The organic layer was washed with brine, dried over sodium sulfate, and concentrated to dryness in vacuo. The crude product was purified by chromatography (silica gel, gradient elution, 20-80% ethyl acetate/hexane) to afford 4.0 g of 5-(4-fluorobenzoyl)-6-hydroxy-2-naphthalenesulfonamide as a solid (83% yield).

Workup

  1. extractionthe product was extracted into methylene chloride
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to dryness in vacuo
  5. customThe crude product was purified by chromatography (silica gel, gradient elution, 20-80% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2898a5411e9140d6b911f03ab864412a
Source dataset
uspto-grants-2000_11
Patent number
US06150397

Reaction notes

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