Trimethyl borate → 3-Ethoxy-4-fluorobenzeneboronic acid

HRID 1515507

Reaktionsgleichung

Reaktionsgleichung von HRID 1515507
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([O:9][CH2:10][CH3:11])[CH:3]=1.[Li]CCCC.[B:17](OC)([O:20]C)[O:18]C>C1COCC1>[CH2:10]([O:9][C:4]1[CH:3]=[C:2]([B:17]([OH:20])[OH:18])[CH:7]=[CH:6][C:5]=1[F:8])[CH3:11]

Komponenten

5

Edukt 3

HCID 8470Trimethyl borateHCID 598380294-Bromo-2-ethoxy-1-fluorobenzeneHCID 178418339Butyllithium

Produkt 1

HCID 445581743-Ethoxy-4-fluorobenzeneboronic acidAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 9A (3.86 g, 17.6 mmol) in THF (60 mL) at −78° C. was added n-BuLi (1.6 M in hexanes, 14.3 mL, 22.8 mmol). The mixture was stirred at −78° C. for 40 min before trimethyl borate (3.63 mL, 33 mmol) was added. The reaction was left stirring from −78° C. to rt over 4 h. It was quenched with 1.0 N HCl (40 mL), extracted with EtOAc, washed with brine and dried over Na2SO4. After evaporation of the solvent, the crude solid product was triturated with EtOAc/hexanes (1:4). After filtration, 9B (2.2 g, 69% yield) was collected as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 1.42 (t, J=7.03 Hz, 3H) 4.11 (q, J=7.03 Hz, 2H) 7.03 (dd, J=11.42, 8.35 Hz, 1H) 7.18-7.29 (m, 2H) 7.35 (d, J=7.91 Hz, 1H).

Aufarbeitung

  1. additionwas added
  2. waitThe reaction was left
  3. customIt was quenched with 1.0 N HCl (40 mL)
  4. extractionextracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. customAfter evaporation of the solvent
  8. customthe crude solid product was triturated with EtOAc/hexanes (1:4)

Quellen und Nachweise

ORD-Eintrag
ord-f451a95260c146d8bd02c6da25e347df
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222453B2

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