Boron tribromide → 4-Fluoro-5-(piperidine-1-sulfonyl)-benzene-1,2-diol

HRID 2103138Notes

Reaction equation

HRID 2103138 reaction equation
B(Br)(Br)Br.[F:5][C:6]1[CH:11]=[C:10]([O:12]C)[C:9]([O:14]C)=[CH:8][C:7]=1[S:16]([N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)(=[O:18])=[O:17].P([O-])(O)(O)=O.[K+]>ClCCl>[F:5][C:6]1[CH:11]=[C:10]([OH:12])[C:9]([OH:14])=[CH:8][C:7]=1[S:16]([N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)(=[O:17])=[O:18]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516951Monobasic potassium phosphateHCID 224750541-(2-Fluoro-4,5-dimethoxy-benzenesulfonyl)-piperidine

Product 1

HCID 224750784-Fluoro-5-(piperidine-1-sulfonyl)-benzene-1,2-diolYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 1M solution of boron tribromide in dichloromethane (58 mL) was added dropwise to a cooled solution of 1-(2-fluoro-4,5-dimethoxy-benzenesulfonyl)-piperidine (5.89 g, 19.42 mmol) in dichloromethane (100 mL), maintaining the temperature between 10 and 20° C. The mixture was stirred overnight at room temperature and poured into 1M aqueous potassium dihydrogenphosphate and ice. After stirring 1 h, the phases were separated and the aqueous phase extracted with ethyl acetate. The combined organic phases were washed with brine, dried over magnesium sulfate and evaporated. The residue was purified by column chromatography on silica gel (10:1 dichloromethane/methanol eluant) to afford the title compound as a brown gum (4.17 g, 78%)

Workup

  1. temperaturemaintaining the temperature between 10 and 20° C
  2. stirringAfter stirring 1 h
  3. customthe phases were separated
  4. extractionthe aqueous phase extracted with ethyl acetate
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe residue was purified by column chromatography on silica gel (10:1 dichloromethane/methanol eluant)

Sources & evidence

ORD record
ord-f8a7f59b0d4340668e15750a82b0532d
Source dataset
uspto-grants-2009_08
Patent number
US07576088B2

Reaction notes

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