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

HRID 335680Notes

Reaction equation

HRID 335680 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>O>[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

4

Reactant 2

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

Product 1

HCID 574756332-Bromo-7-methoxy-9H-xanthen-9-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Sulfuric acid (41 ml, 765 mmol) was added to 2-(4-bromophenoxy)-5-methoxybenzoic acid (3750 mg, 12 mmol) at RT. The reaction mixture was stirred at 60° C. for 60 min. LCMS showed complete reaction. The reaction mixture was cooled to rt and poured slowly over stirred mixture of ice and water (100 ml). The tan precipitate was filtered and washed with water (3×30 ml), twice with 30 ml of 0.5N NaOH, and with water again. The residue was recrystallized from 40 ml THF to give the title compound. MS m/z=307.2 [M+H]+. Calc'd for C14H9BrO3: 305.1.

Workup

  1. customreaction
  2. temperatureThe reaction mixture was cooled to rt
  3. additionpoured slowly
  4. stirringover stirred
  5. filtrationThe tan precipitate was filtered
  6. washwashed with water (3×30 ml), twice with 30 ml of 0.5N NaOH
  7. customThe residue was recrystallized from 40 ml THF

Sources & evidence

ORD record
ord-bfc13b2b01334942bfaba1a5a8706240
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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