Water → 3-Bromobenzanthrone

HRID 2082926Notes

Reaction equation

HRID 2082926 reaction equation
[Br:1]Br.[CH:3]1[C:19]2=[C:20]3[C:10]([C:11]([C:13]4[C:18]2=[CH:17][CH:16]=[CH:15][CH:14]=4)=[O:12])=[CH:9][CH:8]=[CH:7][C:6]3=[CH:5][CH:4]=1.O>C(O)(=O)C>[Br:1][C:5]1[CH:4]=[CH:3][C:19]2[C:18]3[C:13]([C:11](=[O:12])[C:10]4[C:20]=2[C:6]=1[CH:7]=[CH:8][CH:9]=4)=[CH:14][CH:15]=[CH:16][CH:17]=3

Participants

5

Reactant 3

HCID 962WaterHCID 6697BenzanthroneHCID 24408Bromine

Product 1

HCID 66963-BromobenzanthroneYield 68.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of 11.2 g of bromine in 20.5 g of acetic acid was added dropwise to a mixture of 11.5 g of benzanthrone, 184 g of acetic acid and 23 g of water with stirring. The total mixture was heated with stirring to 100° C for 5.5 hours. The precipitated crystals were filtered and washed with water and dried. The product was recrystallized from a mixture of 88.3 g of chlorobenzene and 6.3 g of methanol whereby 10.52 g of 3-bromobenzanthrone were obtained.

Workup

  1. temperatureThe total mixture was heated
  2. stirringwith stirring to 100° C for 5.5 hours
  3. filtrationThe precipitated crystals were filtered
  4. washwashed with water
  5. customdried
  6. customThe product was recrystallized from a mixture of 88.3 g of chlorobenzene

Sources & evidence

ORD record
ord-a0934f089dd144dd8e33f863d830a7b1
Source dataset
uspto-grants-1978_04
Patent number
US04083725

Reaction notes

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