Tetrabutylammonium Fluoride → 2-Chloro-5-[4-(2-hydroxy-ethoxy)-benzoyl]-benzenesulfonamide

HRID 873642Notes

Reaction equation

HRID 873642 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][O:9][C:10]1[CH:28]=[CH:27][C:13]([C:14]([C:16]2[CH:17]=[CH:18][C:19]([Cl:26])=[C:20]([S:22]([NH2:25])(=[O:24])=[O:23])[CH:21]=2)=[O:15])=[CH:12][CH:11]=1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.O>[Cl:26][C:19]1[CH:18]=[CH:17][C:16]([C:14](=[O:15])[C:13]2[CH:12]=[CH:11][C:10]([O:9][CH2:8][CH2:7][OH:6])=[CH:28][CH:27]=2)=[CH:21][C:20]=1[S:22]([NH2:25])(=[O:24])=[O:23]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 668504935-{4-[2-(tert-Butyl-dimethyl-silanyloxy)-ethoxy]-benzoyl}-2-chloro-benzenesulfonamide

Product 1

HCID 442357402-Chloro-5-[4-(2-hydroxy-ethoxy)-benzoyl]-benzenesulfonamideYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-{4-[2-(tert-Butyl-dimethyl-silanyloxy)-ethoxy]-benzoyl}-2-chloro-benzenesulfonamide (1.84 g, 3.92 mmol) is dissolved in tetrahydrofuran (50 mL), and treated with a solution of tetrabutylammonium fluoride reagent (1 M in tetrahydrofuran, 2.2 mmol). The reaction is allowed to stir for 1 hour. The reaction is diluted with water and extracted with ether. The organic phase is separated and concentrated in vacuo affording 1.39 g (100% yield) of the title compound. 1H NMR (DMSO) 3.75 (t, 2H, J=4.55 Hz), 4.12 (t, 2H, J=4.80 Hz), 4.95 (s, 2H), 7.12 (d, 2H, J=8.84 Hz), 7.76-7.90 (m, 4H), 8.24 (d, 1H, J=2.02). MS (m/z): 354 (M−1).

Workup

  1. extractionextracted with ether
  2. customThe organic phase is separated
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9b47852fef47499d8b3473024e8725c4
Source dataset
uspto-grants-2015_03
Patent number
US08975439B2

Reaction notes

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