Ethanol → Ethyl 6-bromonaphthalene-2-carboxylate

HRID 618057Notes

Reaction equation

HRID 618057 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([OH:14])=[O:13])[CH:6]=[CH:5]2.[CH2:15](O)[CH3:16].S(=O)(=O)(O)O>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:6]=[CH:5]2

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 45498526-Bromo-2-naphthalenecarboxylic acid2×

Product 1

HCID 1249959Ethyl 6-bromonaphthalene-2-carboxylate

Procedure

To a solution of 6-bromo-2-naphthalenecarboxylic acid (Compound M) 3.1 g, (12.43 mmol) in ethanol (30 ml, 23.55 g, 511.0 mmol) was added 18M sulfuric acid (2 ml). The solution was refluxed for 30 minutes, cooled to room temperature, and the reaction mixture partitioned between pentane (100 ml) and water (100 ml). The aqueous phase was extracted with pentane (100 ml) and the combined organic layers washed with saturated aqueous NaCl (100 ml), dried (MgSO4), and concentrated to yield an off-white solid. Purification by flash.chromatography (silica, 10% EtOAc-hexane) afforded the title compound as a white solid. 1H NMR (CDCl3): δ 8.58 (1H, br s), 8.10 (1H, dd, J=1.7, 9 Hz), 8.06 (1H, d, J=2 Hz), 7.83 (1H, d, J=9 Hz), 7.80 (1H, d, J=9 Hz), 7.62 (1H, dd, J=2, 9 Hz).

Workup

  1. temperatureThe solution was refluxed for 30 minutes
  2. customthe reaction mixture partitioned between pentane (100 ml) and water (100 ml)
  3. extractionThe aqueous phase was extracted with pentane (100 ml)
  4. washthe combined organic layers washed with saturated aqueous NaCl (100 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customto yield an off-white solid
  8. customPurification by flash.chromatography (silica, 10% EtOAc-hexane)

Sources & evidence

ORD record
ord-429bbd76cd2347c6b4fdaa39371689c7
Source dataset
uspto-grants-1999_09
Patent number
US05952345

Reaction notes

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