1,8-dibromoanthraquinone → 1,8-Dibromoanthracene
Reaction equation
[Br:1][C:2]1[C:15]2[C:14](=O)[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]=3[Br:17])[C:7](=O)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[Br:1][C:2]1[C:15]2[C:6](=[CH:7][C:8]3[C:13]([CH:14]=2)=[C:12]([Br:17])[CH:11]=[CH:10][CH:9]=3)[CH:5]=[CH:4][CH:3]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
23.6 g (65 mmol) of 1,8-dibromoanthraquinone were suspended in 250 ml of methanol. At 10° C., 9.9 g (260 mmol) of NaBH4 were added slowly and the mixture was subsequently stirred at 0° C. for 2 hours. The mixture was poured onto 800 ml of ice, stirred and filtered under reduced pressure. The solid was subsequently suspended in 400 ml of 18% strength hydrochloric acid and stirred at 70° C. for 5 hours, after which it was once again filtered off under reduced pressure, washed until neutral and dried. The solid was stirred with 14.8 g of NaBH4 in 250 ml of isopropanol at 85° C. (reflux) for 3 hours, brought to a pH of 7 by addition of dilute hydrochloric acid, filtered off with suction and washed with water. 1,8-Dibromoanthracene was obtained in a yield of 16.2 g (74% of theory).
Workup
- stirringstirred
- filtrationfiltered under reduced pressure
- stirringstirred at 70° C. for 5 hours
- filtrationafter which it was once again filtered off under reduced pressure
- washwashed until neutral and
- customdried
- stirringThe solid was stirred with 14.8 g of NaBH4 in 250 ml of isopropanol at 85° C.
- temperature(reflux) for 3 hours
- additionbrought to a pH of 7 by addition of dilute hydrochloric acid
- filtrationfiltered off with suction
- washwashed with water
Sources & evidence
- ORD record
- ord-cffde08d9a5b4d3d8bbd90c52250cfbf
- Source dataset
- uspto-grants-2007_02
- Patent number
- US07173138B2
Reaction notes
Loading…