Sulfuric Acid → HCID 67107751, compound

HRID 2177837Notes

Reaction equation

HRID 2177837 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]=1[C:12]([O:14][CH3:15])=[O:13].FC(F)(F)C(O)=O.[Br:23]N1C(C)(C)C(=O)N(Br)C1=O.S(=O)(=O)(O)O.C([O-])(=O)C.[Na+]>C(O)(=O)C>[Br:23][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[C:3]([C:12]([O:14][CH3:15])=[O:13])=[C:2]([CH3:1])[CH:11]=[CH:10]2

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 6422Trifluoroacetic acidHCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 517045Sodium AcetateHCID 10954574HCID 10954574, compound

Product 1

HCID 67107751HCID 67107751, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 2-methylnaphthalene-1-carboxylate (5.6 g) was dissolved in acetic acid (12 ml) and trifluoroacetic acid (12 ml) and cooled in an ice bath. 1,3-Dibromo-5,5-dimethylhydantoin (4.8 g) was added in one portion then concentrated sulphuric acid was added dropwise. The mixture was then stirred at 0° C. for 30 minutes. Sodium acetate (6.12 g) was added and the mixture was partitioned between DCM and water. The organic layer was separated, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of DCM and pentane with a gradient of 20-70% to give methyl 8-bromo-2-methylnaphthalene-1-carboxylate (3.27 g) as a colourless oil.

Workup

  1. customthe mixture was partitioned between DCM and water
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness
  6. customthe residue was purified by chromatography on silica
  7. washeluting with a mixture of DCM and pentane with a gradient of 20-70%

Sources & evidence

ORD record
ord-9d3d2f1ec6fb41eca9b61ed88316df08
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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