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