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

HRID 1396534노트

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HRID 1396534 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8078Cyclohexane용매

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온도
40 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5006a6a9c26b4d71ae57c5ea0b9f1068
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901123B2

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