Ethanol → Ethyl 6-bromonaphthalene-2-carboxylate

HRID 1059799Notes

Reaction equation

HRID 1059799 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-f3984b8109d74deaaed6b29d308fb952
Source dataset
uspto-grants-2003_02
Patent number
US06521624B1

Reaction notes

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