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 11/2 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 1 N NaOH, then brine, separated, dried (MgSO4), filtered and evaporated affording the desired product (4.26 g).

1. temperaturethe reaction refluxed for 11/2 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 1 N NaOH
10. custombrine, separated
11. dry with materialdried (MgSO4)
12. filtrationfiltered
13. customevaporated

ORD record

ord-4197aac4198b4a6d9412db81506fed21

Source dataset

uspto-grants-1992_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05140040