Reaktion #944477

Reaktionsgleichung

tri-isopropoxy borane

(5-bromo-2-fluoro-phenyl)-methanol

n-BuLi

→

desired compound

4-Fluoro-3-hydroxymethyl benzene boronic acid

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm slowly to room temperature
2. 2
   workup.STIRRINGstirred an extra hour
3. 3
   SonstigeThe reaction was quenched with HCl (10%)
4. 4
   Extraktionextracted with EtOAc (2×)
5. 5
   WaschenThe combined organic extracts were washed with brine
6. 6
   Trocknendried over MgSO4
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated
9. 9
   workup.DISSOLUTIONThe residue was dissolved in EtOAc
10. 10
    workup.ADDITIONwater (few drops) was added
11. 11
    Sonstigehexane until a precipitate formed
12. 12
    workup.STIRRINGAfter 12 h of stirring

Vorschrift

To solution of (5-bromo-2-fluoro-phenyl)-methanol (1.0 eq) in THF (0.1M) at −78° C. was added dropwise n-BuLi (2.5M in Hex; 2.2 eq). The resulting mixture was stirred at −78° C. for 30 min then tri-isopropoxy borane (2.2 eq) was added. The final mixture was stirred 15 min at −78° C. then allowed to warm slowly to room temperature and stirred an extra hour. The reaction was quenched with HCl (10%) and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. The residue was dissolved in EtOAc, water (few drops) was added then hexane until a precipitate formed. After 12 h of stirring, the desired compound was isolated by filtration as a white solid.

Quelle