Acetic Acid → 2,7-Dibromo-9,10-dimethylphenanthrene

HRID 550332Notes

Reaction equation

HRID 550332 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][C:9]([Br:16])=[CH:10][CH:11]=3)[CH:6](O)[C:5](C)([CH3:18])[C:4]=2[CH:3]=1.II.Br.[C:23](O)(=O)C>>[Br:16][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[C:4](=[CH:3][C:2]([Br:1])=[CH:15][CH:14]=3)[C:5]([CH3:18])=[C:6]([CH3:23])[C:7]=2[CH:8]=1

Participants

5

Reactant 4

HCID 176Acetic Acid2×HCID 260Hydrogen BromideHCID 807IodineHCID 58963568HCID 58963568, compound

Product 1

HCID 231167462,7-Dibromo-9,10-dimethylphenanthrene

Procedure

43.4 g (113 mmol) of 2,7-dibromo-9-hydroxy-10,10-dimethyl-9,10-dihydrophenanthrene were suspended in 610 ml of acetic acid. 780 mg of iodine and 3.5 ml of HBr in acetic acid were added, and the suspension was heated to reflux. The mixture was allowed to cool overnight with stirring. The residue was filtered off with suction and washed with water and methanol, giving 35.8 g (87.0% of theory) of the product.

Workup

  1. temperaturethe suspension was heated to reflux
  2. temperatureto cool overnight
  3. filtrationThe residue was filtered off with suction
  4. washwashed with water and methanol
  5. customgiving 35.8 g (87.0% of theory) of the product

Sources & evidence

ORD record
ord-9b33bf3061df4918aeae2c287b335405
Source dataset
uspto-grants-2011_05
Patent number
US07947382B2

Reaction notes

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