Oxalyl chloride → 5-Bromo-1,2,3,4-tetrahydronaphthalen-1-one
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][CH2:10][C:11]([OH:13])=O.C(Cl)(=O)C(Cl)=O>C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[CH2:8][CH2:9][CH2:10][C:11]2=[O:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
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 1N NaOH, then brine, separated, dried (MgSO4), filtered and evaporated affording the desired product (4.26 g).