Reacción #2017433

Ecuación de reacción

methyl 6-bromo-2-naphthoate

THF

lithium hydroxide hydrate

→

title compound

6-bromo-2-naphthoic Acid

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónConcentrated under vacuum
2. 2
   workup.ADDITIONdiluted with water
3. 3
   Temperaturacooled to 0° C
4. 4
   FiltraciónSolids were collected by filtration
5. 5
   workup.DISSOLUTIONdissolved in toluene-EtOAc (ca. 2 L)
6. 6
   Lavadowashed with brine
7. 7
   SecadoDried over Na2SO4
8. 8
   Filtraciónfiltered
9. 9
   Concentraciónconcentrated under vacuum
10. 10
    OtroBrown solid was triturated with ether
11. 11
    Filtracióncollected by filtration
12. 12
    Otrodried under vacuum

Procedimiento

A solution of methyl 6-bromo-2-naphthoate (7.70 g, 29.0 mmol) in 2:1 THF:water (150 mL) was treated with lithium hydroxide hydrate (2.44 g, 58.1 mmol) followed by stirring at room temperature for 48 h. Concentrated under vacuum, diluted with water and cooled to 0° C. Acidified to pH3 with 4N HCl. Solids were collected by filtration, dissolved in toluene-EtOAc (ca. 2 L) and washed with brine. Dried over Na2SO4, filtered and concentrated under vacuum. Brown solid was triturated with ether, collected by filtration, and dried under vacuum to give the title compound as a nearly white solid (5.07 g, 70%).

Fuente