Hydrochloric Acid → (4-Formylthiophen-3-yl)boronic acid

HRID 1714042

反応式

HRID 1714042 の反応式
[B:1](OC(C)C)([O:6]C(C)C)[O:2]C(C)C.Br[C:15]1[C:16]([CH:20]2[O:24]CCO2)=[CH:17][S:18][CH:19]=1.[Li]CCCC.Cl>C1(C)C=CC=CC=1.C1COCC1>[CH:20]([C:16]1[C:15]([B:1]([OH:6])[OH:2])=[CH:19][S:18][CH:17]=1)=[O:24]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 12284898HCID 12284898、化合物HCID 178418339Butyllithium

生成物 1

HCID 4190637(4-Formylthiophen-3-yl)boronic acid収率 95%

試薬・触媒・溶媒 1

HCID 22635083Tetrahydrofuran toluene溶媒2 回

反応条件

温度
-78 °C

実験手順

To a 0.5M solution of B(Oi-Pr)3 (1.2 eq) in toluene/THF 4:1 was added a solution of 2-(4-bromo-3-thienyl)-1,3-dioxolane in toluene/THF 4:1, and the mixture was then cooled to −78° C. BuLi (1.5M in hexanes; 1.2 eq) was then added over 1 h, and the solution kept at this temperature for an additional h, then allowed to warm to −20° C. over 3 h; aq 1N HCl was added and the mixture stirred for an additional h at this temperature. Removal of volatiles gave an aqueous solution that was extracted with DCM; the combined organic phases were then washed with brine, dried over Na2SO4 and concentrated in vacuo. Yield: 95%.

後処理

  1. temperatureto warm to −20° C. over 3 h
  2. customRemoval of volatiles
  3. customgave an aqueous solution that
  4. extractionwas extracted with DCM
  5. washthe combined organic phases were then washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-a0f53afc9c454528be29c1e7c46f6753
出典データセット
uspto-grants-2010_09
特許番号
US07795247B2

関連ノート

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