Tetrabutylammonium Fluoride → 2-Chloro-5-(3-hydroxy-4-methoxy-benzoyl)-benzenesulfonamide

HRID 873639Notes

Reaction equation

HRID 873639 reaction equation
C([Si](C)(C)[O:6][C:7]1[CH:8]=[C:9]([CH:23]=[CH:24][C:25]=1[O:26][CH3:27])[C:10]([C:12]1[CH:13]=[CH:14][C:15]([Cl:22])=[C:16]([S:18]([NH2:21])(=[O:20])=[O:19])[CH:17]=1)=[O:11])(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[Cl:22][C:15]1[CH:14]=[CH:13][C:12]([C:10](=[O:11])[C:9]2[CH:23]=[CH:24][C:25]([O:26][CH3:27])=[C:7]([OH:6])[CH:8]=2)=[CH:17][C:16]=1[S:18]([NH2:21])(=[O:20])=[O:19]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 581075125-[3-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-benzoyl]-2-chloro-benzenesulfonamide

Product 1

HCID 581074722-Chloro-5-(3-hydroxy-4-methoxy-benzoyl)-benzenesulfonamideYield 52.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5-[3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-benzoyl]-2-chloro-benzenesulfonamide (0.28 g, 0.61 mmol) dissolved in tetrahydrofuran (20 mL) is added 1 M tetrabutylammonium fluoride (1.23 mL, 1.22 mmol) in tetrahydrofuran. The reaction mixture is stirred at room temperature for 30 minutes. The reaction is quenched with 1 N of HCl, and extracted with ethyl acetate three times. The combined organic extracts are washed with a saturated sodium chloride solution, dried with magnesium sulfate, and concentrated in vacuo. Recrystallization from ethyl acetate/methylene chloride provides 0.11 g (49%) of the title compound as a brown solid. 1H NMR (DMSO): δ 9.60 (s, 1H), 8.20 (d, J=2 Hz, 1H), 7.80 (m, 4H), 7.20 (m, 2H), 7.10 (d, J=8 Hz, 1H), 3.90 (s, 3H). Analytics calculated for C14H12ClNO5S: C, 49.20; H, 3.54; N, 4.10. Found: C, 49.90; H, 3.30; N, 5.06. MS (m/z): 342 (M+1).

Workup

  1. customThe reaction is quenched with 1 N of HCl
  2. extractionextracted with ethyl acetate three times
  3. washThe combined organic extracts are washed with a saturated sodium chloride solution
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customRecrystallization from ethyl acetate/methylene chloride

Sources & evidence

ORD record
ord-9905e06bfc474d2a9102be3964059a83
Source dataset
uspto-grants-2015_03
Patent number
US08975439B2

Reaction notes

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