Sulfuric Acid → HCID 86723697, compound

HRID 577467Notes

Reaction equation

HRID 577467 reaction equation
[CH3:1][C:2]1[C:10]([O:11][CH:12]([CH3:14])[CH3:13])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Br:15]Br.OS(O)(=O)=O>CC(O)=O.CO>[Br:15][C:7]1[C:3]([C:4]([OH:6])=[O:5])=[C:2]([CH3:1])[C:10]([O:11][CH:12]([CH3:14])[CH3:13])=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 24408BromineHCID 68722114HCID 68722114, compound

Product 1

HCID 86723697HCID 86723697, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of 2-methyl-3-(propan-2-yloxy)benzoic acid (Cpd NN, 1.08 g, 5.56 mmol) in AcOH (5 mL) was added Br2 (888 mg, 5.56 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated under vacuum to give an oil. The crude oil was dissolved in MeOH (20 mL) then H2SO4 was added and the resulting mixture was heated at 65° C. for 2 hours. The reaction mixture was concentrated under vacuum and the residue dissolved in EtOAc. The organic layer was washed with water and brine, dried with Na2SO4, and concentrated under vacuum to give 6-bromo-2-methyl-3-(propan-2-yloxy)benzoic acid (Cpd OO, 1.3 g, 86%) as an oil which solidified to a tan solid upon standing.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customto give an oil
  3. temperaturethe resulting mixture was heated at 65° C. for 2 hours
  4. concentrationThe reaction mixture was concentrated under vacuum
  5. dissolutionthe residue dissolved in EtOAc
  6. washThe organic layer was washed with water and brine
  7. dry with materialdried with Na2SO4
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-823015ed191246dd9c8e5fe701c724f2
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

Loading…