Sulfuric Acid → 2-Bromo-7-methoxy-9H-xanthen-9-one

HRID 931536Notes

Reaction equation

HRID 931536 reaction equation
S(=O)(=O)(O)O.[Br:6][C:7]1[CH:24]=[CH:23][C:10]([O:11][C:12]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:13]=2[C:14]([OH:16])=O)=[CH:9][CH:8]=1>>[Br:6][C:7]1[CH:8]=[CH:9][C:10]2[O:11][C:12]3[C:13](=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=3)[C:14](=[O:16])[C:23]=2[CH:24]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 574756322-(4-Bromophenoxy)-5-methoxybenzoic acid

Product 1

HCID 574756332-Bromo-7-methoxy-9H-xanthen-9-oneYield 259.8%

Conditions

Temperature
60 °C

Procedure

Sulfuric acid (1.6 L) was added to 2-(4-bromophenoxy)-5-methoxybenzoic acid (530 g, 1.6401 mol) at RT. The resulting dark mixture was heated to 60° C. for 1 hour. The brown solution was cooled to RT and poured onto ice while stirring. The resulting tan precipitate was collected by filtration, washed sequentially with water (2 L), 1N NaOH (2.0 L) and ethanol (800 mL). The derived solid was suspended in 2 L of acetone and stirred vigorously for 1 hour. The mixture was filtered and dried under a vacuum to afford 1.3 kg of 2-bromo-7-methoxy-9H-xanthen-9-one as a white solid.

Workup

  1. temperatureThe brown solution was cooled to RT
  2. additionpoured onto ice
  3. filtrationThe resulting tan precipitate was collected by filtration
  4. washwashed sequentially with water (2 L), 1N NaOH (2.0 L) and ethanol (800 mL)
  5. stirringstirred vigorously for 1 hour
  6. filtrationThe mixture was filtered
  7. customdried under a vacuum

Sources & evidence

ORD record
ord-81b89011b5524062aa8be938390efb44
Source dataset
uspto-grants-2016_03
Patent number
US09296759B2

Reaction notes

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