Pinacol → 2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

HRID 1396534ノート

反応式

HRID 1396534 の反応式
[F:1][C:2]1[CH:3]=[C:4]([B:10]([OH:12])[OH:11])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].O[C:14]([C:17](O)([CH3:19])[CH3:18])([CH3:16])[CH3:15]>C1CCCCC1>[F:1][C:2]1[CH:3]=[C:4]([B:10]2[O:12][C:17]([CH3:19])([CH3:18])[C:14]([CH3:16])([CH3:15])[O:11]2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

参加物

4

反応物 2

HCID 6425PinacolHCID 2783130(4-Cyano-3-fluorophenyl)boronic acid

生成物 1

HCID 513509512-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile収率 85.6%

試薬・触媒・溶媒 1

HCID 8078Cyclohexane溶媒

反応条件

温度
40 °C

実験手順

A suspension of the crude 3-fluoro-4-cyanophenyl boronic acid (9.2 Kg, 55.8 mol) in cyclohexane (150 L) was treated with pinacol (13.2 Kg, 111.6 mol, 2.0 equiv) at room temperature, and the resulting reaction mixture was warmed to 40° C. for 4 h. When TLC and LC/MS showed that the reaction was deemed complete, the reaction mixture was cooled down to room temperature before being washed with water (2×75 L). The organic layer was then dried over magnesium sulfate (MgSO4) and concentrated under the reduced pressure to afford 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (19, 11.8 Kg, 13.8 Kg theoretical, 85.6% yield) as a light yellow solid. For 19: 1H NMR (300 MHz, DMSO-d6) δ ppm 7.92 (t, 1H, J=7.00 Hz), 7.62 (m, 2H), 1.29 (s, 12H).

後処理

  1. customthe resulting reaction mixture
  2. temperaturethe reaction mixture was cooled down to room temperature
  3. washbefore being washed with water (2×75 L)
  4. dry with materialThe organic layer was then dried over magnesium sulfate (MgSO4)
  5. concentrationconcentrated under the reduced pressure

出典と根拠

ORDレコード
ord-5006a6a9c26b4d71ae57c5ea0b9f1068
出典データセット
uspto-grants-2014_12
特許番号
US08901123B2

反応ノート

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