Sulfuric Acid → HCID 57475644, compound

HRID 931551Notes

Reaction equation

HRID 931551 reaction equation
OS(O)(=O)=O.[Br:6][C:7]1[CH:23]=[CH:22][C:10]([O:11][C:12]2[CH:20]=[CH:19][C:18]([I:21])=[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]([I:21])=[CH:19][CH:20]=3)[C:14](=[O:16])[C:22]=2[CH:23]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 57475643HCID 57475643, compound

Product 1

HCID 57475644HCID 57475644, compoundYield 84.9%

Conditions

Temperature
60 °C

Procedure

H2SO4 (73.3 ml, 1375 mmol) was added to 2-(4-bromophenoxy)-5-iodobenzoic acid (28.800 g, 68.7 mmol) at rt. The resulting dark mixture was heated to 60° C. for 45 minutes. The brown solution was poured slowly onto ice-water (1 L) with stirring. The resulting tan precipitant was collected by filtration, washed with water a 1 N solution of NaOH, again with water, and dried under reduced pressure to afford 2-bromo-7-iodo-9H-xanthen-9-one (23.4 g) as a tan solid that was used without further purification.

Workup

  1. additionThe brown solution was poured slowly onto ice-water (1 L)
  2. filtrationThe resulting tan precipitant was collected by filtration
  3. washwashed with water a 1 N solution of NaOH
  4. dry with materialagain with water, and dried under reduced pressure

Sources & evidence

ORD record
ord-2f6353afd16b48b8a8136f9e8c23174e
Source dataset
uspto-grants-2016_03
Patent number
US09296759B2

Reaction notes

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