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

HRID 1052508ノート

反応式

HRID 1052508 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-0b1089e3130c4f0199df94d557058a90
出典データセット
uspto-grants-2016_07
特許番号
US09388189B2

反応ノート

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