Methanol → 1-(4-Bromo-2-fluorophenyl)ethan-1-amine

Temperatur

0 °C

To a solution of 12 g of 4-bromo-2-fluorobenzonitrile (60 mM) in THF (120 ml) were added 75 ml (150 mM) of a 2 M solution of methylmagnesium bromide in diethyl ether at 0° C. The reaction mixture was stirred at 0° C. for 6 h. Then 200 ml of methanol were added gradually to the reaction mixture. Subsequently, 5.7 g (150 mM) of sodium borohydride were added in portions, and the mixture was stirred at room temperature for 16 h. Thereafter, the reaction mixture was concentrated under reduced pressure, and 200 ml of water were added. The pH was adjusted to pH=˜1 with 2 M HCl, and the aqueous solution was extracted with chloroform. Subsequently, the pH was adjusted to pH=˜9 with 2M NaOH, and extraction was effected with chloroform (2×100 ml). The combined chloroform extracts were dried, and the solvent was removed under reduced pressure. 7.3 g (44%) of 1-(4-bromo-2-fluorophenyl)ethanamine were obtained as a yellow oil.

1. stirringthe mixture was stirred at room temperature for 16 h
2. concentrationThereafter, the reaction mixture was concentrated under reduced pressure, and 200 ml of water
3. additionwere added
4. extractionthe aqueous solution was extracted with chloroform
5. extractionSubsequently, the pH was adjusted to pH=˜9 with 2M NaOH, and extraction
6. dry with materialThe combined chloroform extracts were dried
7. customthe solvent was removed under reduced pressure

ORD-Eintrag

ord-b6bbb2fab1e442519fd838c44c473ea1

Quelldatensatz

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08889878B2