2-Aminophenol → 4-Fluoro-N-(2-hydroxyphenyl)benzamide

Temperatur

60 °C

To a 500 ml 4 necked round bottom flask equipped with a thermometer, a mechanic stirrer, a drop funnel, a nitrogen in-let, was added sodium bicarbonate (29.6 g, 0.354 mol, 1.1 eq), 2-aminophenol (34.88 g, 0.32 mol, 1 eq) and 2-Methyl THF (250 ml). The temperature of the mixture was controlled under 20° C. by ice-bath. Under vigorously stirring, 4-fluorobenzoyl chloride (50.72 g, 0.32 mol, 1 eq) was added drop wise within 10 min. Then the reaction was allowed to be stirred for another 1.5 hrs. When HPLC data showed that less than 0.3% of 2-aminophenol remained, 100 ml of water and 50 ml of 2-methyl tetrahydrofuran was added to quench the reaction and then the mixture was heated to 60° C. with stirring. The mixture was partitioned into two phases and the organic phase was washed with 100 ml of 1N H2SO4 and subsequently with 100 ml of water. Then the solvent was evaporated to almost dryness with stirring.

1. customThe temperature of the mixture was controlled under 20° C. by ice-bath
2. stirringto be stirred for another 1.5 hrs
3. customto quench
4. customthe reaction
5. stirringwith stirring
6. customThe mixture was partitioned into two phases
7. washthe organic phase was washed with 100 ml of 1N H2SO4 and subsequently with 100 ml of water
8. customThen the solvent was evaporated to almost dryness
9. stirringwith stirring

ORD-Eintrag

ord-184b04ec7f5642aabf0759c1f6f1a299

Quelldatensatz

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09440935B2