Water → HCID 58316990, compound

HRID 1187304Notes

Reaction equation

HRID 1187304 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][OH:20])[C:14]=1[F:21])(=[O:11])=[O:10].I(C1C=CC=CC=1C(O)=O)(=O)=O.O>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]=[O:20])[C:14]=1[F:21])(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 962WaterHCID 1087942-Iodoxybenzoic acidHCID 58317006HCID 58317006, compound

Product 1

HCID 58316990HCID 58316990, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,5-Difluoro-N-(2-fluoro-3-hydroxymethyl-phenyl)-benzenesulfonamide (75, 950 mg, 2.99 mmol) and stabilized 2-iodoxybenzoic acid (2.608 g, 45%, 4.2 mmol) are dissolved in 150 mL of tetrahydrofuran and the reaction is stirred at room temperature for 16 hours. The reaction is poured into water and extracted with ethyl acetate. The organic layer is washed with brine, dried over sodium sulfate, filtered and the filtrate is concentrated under vacuum. The resulting material is purified by silica gel column chromatography, eluting with ethyl acetate and dichloromethane. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound (76, 0.944 g). MS (ESI) [M−H+]−=314.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer is washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate is concentrated under vacuum
  6. customThe resulting material is purified by silica gel column chromatography
  7. washeluting with ethyl acetate and dichloromethane
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a88499c8ec3245a1b2b770a31b4f6dab
Source dataset
uspto-grants-2014_03
Patent number
US08673928B2

Reaction notes

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