Hydrochloric Acid → 4-((Methylamino)sulphonyl)benzene boronic acid

HRID 401578

反応式

HRID 401578 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH3:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[B:13](OC(C)C)([O:18]C(C)C)[O:14]C(C)C.[Li]CCCC.Cl>C1COCC1>[CH3:12][NH:11][S:8]([C:5]1[CH:6]=[CH:7][C:2]([B:13]([OH:18])[OH:14])=[CH:3][CH:4]=1)(=[O:10])=[O:9]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 1012154-bromo-N-methylbenzene-1-sulfonamideHCID 178418339Butyllithium

生成物 1

HCID 441187634-((Methylamino)sulphonyl)benzene boronic acid収率 104.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of 4-bromo-N-methyl-benzene sulfonamide (24.9 g, 0.1 mol) and B(OiPr)3 (28.2 g, 0.15 mol) in THF (200 mL) was added n-BuLi (100 mL, 0.25 mol) at −70° C. The mixture was slowly warmed to 0° C., then 10% HCl solution was added until pH 3-4. The resulting mixture was extracted with EtOAc. The organic layer was dried over Na2SO4, and evaporated under reduced pressure to give 4-(N-methylsulfamoyl)phenylboronic acid (22.5 g, 96%), which was used in the next step without further purification. 1H NMR (DMSO-d6, 300 MHz) δ 8.29 (s, 2H), 7.92 (d, J=8.1 Hz, 2H), 7.69 (d, J=8.4 Hz, 2H), 2.36 (d, J=5.1 Hz, 3H).

後処理

  1. extractionThe resulting mixture was extracted with EtOAc
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-2738e480f3324b9b84498b4467f5c964
出典データセット
uspto-grants-2014_06
特許番号
US08741933B2

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