Anthralin → 10-Bromo-1,8-dihydroxy-10H-anthracen-9-one

HRID 1651148Notes

Reaction equation

HRID 1651148 reaction equation
[OH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]=3[OH:17])[CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[Br:18]Br>C(=S)=S>[Br:18][CH:7]1[C:6]2[C:15](=[C:2]([OH:1])[CH:3]=[CH:4][CH:5]=2)[C:14](=[O:16])[C:13]2[C:12]([OH:17])=[CH:11][CH:10]=[CH:9][C:8]1=2

Participants

4

Reactant 2

HCID 2202AnthralinHCID 24408Bromine

Product 1

HCID 27650410-Bromo-1,8-dihydroxy-10H-anthracen-9-oneYield 77.6%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Conditions

Temperature
50 °C

Procedure

1,8-Dihydroxy-9-anthrone (17.3 g) was dissolved in carbon disulphide (1.25 liter) by heating, and the solution was treated dropwise with 18.5 g of bromine with stirring at 50° C. The solution was left stirring at that temperature overnight, then cooled to room temperature and concentrated to one tenth of its volume by removal of the solvent under reduced pressure. The yellow precipitate was filtered off, dried and recrystallised from a petroleum ether (boiling point 40°-60° C.)/chloroform mixture (1:1) to give 10-bromo-1,8-dihydroxy-9-anthrone (18.1 g, 77.5%), melting point 149°-151° C. (with decomposition). [Literature reference, O. E. Schultz and H.-H. Schultze-Mosgau, Arch. Pharm. (Weinheim. Ger.), 1965, 298, 273, gives melting point 148°-150° C. (with decomposition)].

Workup

  1. temperatureby heating
  2. waitThe solution was left
  3. stirringstirring at that temperature overnight
  4. temperaturecooled to room temperature
  5. concentrationconcentrated to one tenth of its volume by removal of the solvent under reduced pressure
  6. filtrationThe yellow precipitate was filtered off
  7. customdried
  8. customrecrystallised from a petroleum ether (boiling point 40°-60° C.)/chloroform mixture (1:1)

Sources & evidence

ORD record
ord-304493862b6749a580e8a0c4f88e0802
Source dataset
uspto-grants-1990_05
Patent number
US04927845

Reaction notes

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