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2-Bromo-4-methoxy-5-(1-methylethoxy)benzeneacetyl Chloride
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Molbank 2002, 2002(1), M294; https://doi.org/10.3390/M294

Short Note
2-Bromo-4-methoxy-5-(1-methylethoxy)benzeneacetic Acid
Institute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9/163OC, A-1060 Vienna, Austria
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Received: 20 December 2001 / Accepted: 8 May 2002 / Published: 27 February 2003
Molbank 2002 m294 i001
2-Bromo-4-methoxy-5-(1-methylethoxy)benzeneacetonitrile [1] (5.86 g, 20.6 mmol) was refluxed in 25% NaOH (50 mL)/EtOH (50 mL) for 12 h. The mixture was concentrated to a volume of 50 mL, the residue was washed with Et2O (2 x 10 mL), and the pH was adjusted to 1 using conc. HCl. The aqueous layer was extracted with Et2O (3 x 50 mL), and the combined organic layer was washed with water (5 x 100 mL) and brine (100 mL), dried over Na2SO4, filtered and concentrated in vacuo. The residue was triturated with iPr2O (2 x 50 mL). Yield: colorless crystals (5.59 g, 90%), mp. 128 - 132 °C.
TLC: petroleum ether : EtOAc = 80 : 30, Rf = 0.1.
Anal. Calcd for C12H15BrO4: C, 47.54; H, 4.99. Found: C, 47.76; H, 4.93.
1H NMR (CDCl3): d 10.10 (b, 1H), 7.02 (s, 1H), 6.81 (s, 1H), 4.47 (septet, J = 6.4 Hz, 1H), 3.82 (s, 3H), 3.71 (s, 2H), 1.32 (d, J = 6.4 Hz, 6H).
13C NMR (CDCl3): d 176.9 (s), 150.3 (s), 146.5 (s), 125.1 (s), 118.4 (d), 116.0 (d), 115.3 (s), 71.8 (d), 56.1 (q), 40.7 (t), 21.9 (q).

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

References and Notes

  1. Treu, M.; Mereiter, K.; Hametner, Ch.; Fröhlich, J.; Jordis, U. Carboxylic Galanthamine Analogs II: 4a,5,9,10,11,12-Hexahydro-6H-benzo[a]cyclohepta[hi]benzofuran. Submitted to J. Heterocyclic Chem.
  • Samples Availability: Available from the authors.
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