Dichloromethane → 2-fluoro-N-hydroxybenzenecarboximidoyl chloride

Temperatur

-10 °C

In 1 liter dichloromethane was dissolved 55.0 g 2-fluorobenzaldehyde oxime at room temperature with stirring. The resulting solution was cooled to -10° C. and Cl2 was bubbled in at such a rate to maintain the temperature below 15° C. After a dark blue color was generated (2-3 minutes) a solution of triethylamine (50 ml) in dichloromethane (100 ml) was added dropwise concurrently with Cl2 addition. When the reaction mixture had maintained a yellow color, additions of the triethylamine solution and Cl2 were discontinued. Concentration of the reaction mixture left an oil which was dissolved in ether and washed four times with 3N HCl followed by a final wash with brine. The organic layer was dried (MgSO4), filtered and concentrated in vacuo to give 60.0 g of 2-fluoro-N-hydroxybenzenecarboximidoyl chloride as an oil which solidified on standing.

1. customCl2 was bubbled in at such a rate
2. temperatureto maintain the temperature below 15° C
3. custom(2-3 minutes)
4. additionwas added dropwise concurrently with Cl2 addition
5. temperatureWhen the reaction mixture had maintained a yellow color, additions of the triethylamine solution and Cl2
6. waitConcentration of the reaction mixture left an oil which
7. dissolutionwas dissolved in ether
8. washwashed four times with 3N HCl
9. washa final wash with brine
10. dry with materialThe organic layer was dried (MgSO4)
11. filtrationfiltered
12. concentrationconcentrated in vacuo

ORD-Eintrag

ord-0ee60752577b406da52bc6fe5f06193a

Quelldatensatz

uspto-grants-1993_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05256672