Triisopropyl borate → (5-Cyano-1-benzothiophen-2-yl)boronic acid

HRID 2173025ノート

反応式

HRID 2173025 の反応式
[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([C:10]#[N:11])[CH:8]=[CH:9][C:2]1=2.C([Li])CCC.[B:17](OC(C)C)([O:22]C(C)C)[O:18]C(C)C>C1COCC1>[C:10]([C:7]1[CH:8]=[CH:9][C:2]2[S:1][C:5]([B:17]([OH:22])[OH:18])=[CH:4][C:3]=2[CH:6]=1)#[N:11]

参加物

5

反応物 3

HCID 21531Triisopropyl borateHCID 27954521-Benzothiophene-5-carbonitrileHCID 178418339Butyllithium

生成物 1

HCID 53398611(5-Cyano-1-benzothiophen-2-yl)boronic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a cold (−78° C.) solution of benzo[b]thiophene-5-carbonitrile (276 mg, 1.734 mmol) in anhydrous THF (5 mL) was added n-butyllithium (0.763 mL, 1.907 mmol) dropwise. The reaction mixture was stirred at −78° C. for 60 minutes. Next, a solution of triisopropyl borate (0.478 mL, 2.080 mmol) was added. The reaction mixture was stirred for 30 minutes stirring at −78° C. and then was allowed to warm to room temperature over a 2 hour period. Solvent was removed to give the title compound, which was used without purification or work up.

後処理

  1. stirringThe reaction mixture was stirred for 30 minutes
  2. stirringstirring at −78° C.
  3. temperatureto warm to room temperature over a 2 hour period
  4. customSolvent was removed

出典と根拠

ORDレコード
ord-c964ed1377204c2e9b6f5bd9586267cd
出典データセット
uspto-grants-2015_06
特許番号
US09056873B2

反応ノート

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