Oxalyl chloride → 5-Bromo-1,2,3,4-tetrahydronaphthalen-1-one

Temperature

0 °C

To a benzene solution (60 ml) of 4-(o- bromophenyl) butyric acid (5 g) was added oxalyl chloride (3.6 ml) and the reaction refluxed for 1 1/2 hrs. The solution was evaporated to dryness, the residue was dissolved in CH2Cl2 (50 ml) then cooled to 0° C., followed by the addition of AlCl3 (3.1 g). The mixture was stirred at 0° C. warming to room temperature overnight. The reaction was poured onto ice, then extracted with CH2Cl2. The organic layer was separated, washed with IN NaOH, then brine, separated, dried (MgSO4), filtered and evaporated affording the desired product (4.26 g).

1. temperaturethe reaction refluxed for 1 1/2 hrs
2. customThe solution was evaporated to dryness
3. dissolutionthe residue was dissolved in CH2Cl2 (50 ml)
4. additionfollowed by the addition of AlCl3 (3.1 g)
5. temperaturewarming to room temperature overnight
6. additionThe reaction was poured onto ice
7. extractionextracted with CH2Cl2
8. customThe organic layer was separated
9. washwashed with IN NaOH
10. custombrine, separated
11. dry with materialdried (MgSO4)
12. filtrationfiltered
13. customevaporated

ORD record

ord-9356601a39c84ef68baab74aecd9d3ea

Source dataset

uspto-grants-1992_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05086074