Sulfuric Acid → Methyl 4-bromo-1-naphthoate

HRID 1950711Notes

Reaction equation

HRID 1950711 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([OH:14])=[O:13])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:20]COC(C)=O.CCCCCCC>CO>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([O:14][CH3:20])=[O:13])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 8900HeptaneHCID 2825914-Bromo-1-naphthoic acid

Product 1

HCID 22711886Methyl 4-bromo-1-naphthoateYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-bromo naphthoic acid (4.0 g, 15.9 mmol) in MeOH (75 mL) was added sulfuric acid (0.5 mL) and the reaction was heated to reflux for 18 hours. TLC 50:50 EtOAc:heptane showed consumption of starting material. The reaction was cooled and concentrated under vacuum to remove MeOH. The residue was diluted with EtOAc (150 mL), washed with water (100 mL), diluted with saturated NaHCO3 (100 mL), dried over Na2SO4 and concentrated under vacuum to afford a solid (3.85 g, 91%). 1H NMR (CDCl3) δ ppm: 8.96 (1H), 8.36 (1H), 8.02 (1H), 7.85 (1H), 7.70-7.66 (2H), 4.03 (3H).

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 18 hours
  3. customconsumption of starting material
  4. temperatureThe reaction was cooled
  5. concentrationconcentrated under vacuum
  6. customto remove MeOH
  7. additionThe residue was diluted with EtOAc (150 mL)
  8. washwashed with water (100 mL)
  9. additiondiluted with saturated NaHCO3 (100 mL)
  10. dry with materialdried over Na2SO4
  11. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-009186cbab0c4dce8d2637a1bd5f336f
Source dataset
uspto-grants-2013_03
Patent number
US08404649B2

Reaction notes

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