Acetic Acid → 3-Bromo-6-chlorophenanthrene-9,10-dione
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:6]=CC3[C:13]([C:14]=2[CH:15]=1)=[CH:12][C:11]([Cl:16])=[CH:10][CH:9]=3.[OH2:17].[C:18]([OH:21])(=O)[CH3:19]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:17])[C:18](=[O:21])[C:19]3[C:13]([C:14]=2[CH:15]=1)=[CH:12][C:11]([Cl:16])=[CH:10][CH:9]=3Participants
4
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 3-bromo-6-chlorophenanthrene from Step 2 (1.71 g; 5.86 mmol) in 35 mL of acetic acid was added 2.3 g (23.5 mmol) of CrO3. The mixture was stirred 2 hrs at 100° C., cooled down to room temperature, poured into 300 mL of water and stirred for 1 hr. The suspension was filtered, washed with water and Et2O and pumped under reduced pressure to afford 1.67 g of 3-bromo-6-chlorophenanthrene-9,10-dione as a solid.