Boron tribromide → (3-(4-Hydroxyphenylsulfonamido)phenyl)boronic acid

HRID 1052508Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1052508
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([B:19]3[O:23]C(C)(C)C(C)(C)[O:20]3)[CH:14]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][C:13]2[CH:14]=[C:15]([B:19]([OH:23])[OH:20])[CH:16]=[CH:17][CH:18]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 901029924-Methoxy-N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzenesulfonamide

Produkt 1

HCID 90103182(3-(4-Hydroxyphenylsulfonamido)phenyl)boronic acidAusbeute 23,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

4-Methoxy-N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzenesulfonamide (168 mg, 0.43 mmol) was dissolved in dichloromethane (4 ml). A solution of boron tribromide (1M in dichloromethane, 4.32 mL, 4.32 mmol) was added dropwise and the reaction was stirred at room temperature overnight. The mixture was diluted with dichloromethane and washed with a solution of 4% sodium bicarbonate, water, brine and dried over sodium sulphate, filtered and evaporated under reduced pressure. The product was purified by reverse phase using SP1® Purification System to give 30 mg (23% yield) of the title compound. Purity 100%.

Aufarbeitung

  1. washwashed with a solution of 4% sodium bicarbonate, water, brine
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe product was purified by reverse phase
  6. custom® Purification System

Quellen und Nachweise

ORD-Eintrag
ord-0b1089e3130c4f0199df94d557058a90
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09388189B2

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