Acetic Acid → 3-Bromo-6-chlorophenanthrene-9,10-dione

HRID 2117980Notes

Reaction equation

HRID 2117980 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]=3

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 445415223-Bromo-6-chlorophenanthrene

Product 1

HCID 167388333-Bromo-6-chlorophenanthrene-9,10-dione

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.

Workup

  1. temperaturecooled down to room temperature
  2. stirringstirred for 1 hr
  3. filtrationThe suspension was filtered
  4. washwashed with water and Et2O

Sources & evidence

ORD record
ord-e60b9c9e9d844674aa2599a6b14f430c
Source dataset
uspto-grants-2008_10
Patent number
US07442716B2

Reaction notes

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