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

HRID 1052508노트

반응식

HRID 1052508 반응식
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

참가 물질

4

반응물 2

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

생성물 1

HCID 90103182(3-(4-Hydroxyphenylsulfonamido)phenyl)boronic acid수율 23.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-0b1089e3130c4f0199df94d557058a90
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09388189B2

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