Triisopropyl borate → 4-Bromo-3-isopropylanisole

HRID 237817Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 237817
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH:10]([CH3:12])[CH3:11].[Li]CCCC.[B:18](OC(C)C)([O:23]C(C)C)[O:19]C(C)C>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH:10]([CH3:12])[CH3:11].[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([B:18]([OH:23])[OH:19])=[C:3]([CH:10]([CH3:12])[CH3:11])[CH:4]=1

Komponenten

5

Edukt 3

HCID 21531Triisopropyl borateHCID 117464064-Bromo-3-isopropylanisoleHCID 178418339Butyllithium

Produkt 2

HCID 117464064-Bromo-3-isopropylanisoleHCID 220217692-Isopropyl-4-methoxyphenyl boronic acid

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

1-Bromo-2-isopropyl-4-methoxy-benzene was prepared in accordance with the procedures of Konishi et. al., Bull. Chem. Soc. Jpn., 1989, 62, 591-593. To a solution of 1-bromo-2-isopropyl-4-methoxy-benzene (4.5 g, 19.7 mmol) was added BuLi (1.6M in hexane, 14.8 mL, 23.7 mmol) at −78° C. The reaction mixture was stirred at −78° C. for 40 min, followed by addition of B(O-iPr)3 dropwise. The resulting mixture was stirred at −78° C. for 2 hours, then warmed to room temperature overnight. The reaction mixture was quenched with HCl (1N) and extracted with diethyl ether three times. The organic phase was washed with water, brine and dried (Na2SO4). Silica gel chromatography (10-30%EtOAc/heptane) provided 2.3 g of 4-methoxy-2-isopropyl-phenylboronic acid.

Aufarbeitung

  1. stirringThe resulting mixture was stirred at −78° C. for 2 hours
  2. temperaturewarmed to room temperature overnight
  3. customThe reaction mixture was quenched with HCl (1N)
  4. extractionextracted with diethyl ether three times
  5. washThe organic phase was washed with water, brine
  6. dry with materialdried (Na2SO4)

Quellen und Nachweise

ORD-Eintrag
ord-8f00441dcb7b449bab4dbdfbdcf34969
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642603B2

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