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Short Note

2,3-Dibromo-2-methyl-5-phenylpentanoic Acid

by
Martin J. Stoermer
* and
John T. Pinhey
Division of Organic Chemistry, School of Chemistry F11, The University of Sydney, N.S.W 2006, Australia
*
Author to whom correspondence should be addressed.
*
Current address: Victorian College of Pharmacy, Monash University (Parkville Campus), 381 Royal Parade, Parkville, Victoria 3052, Australia
Molecules 1998, 3(3), M65; https://doi.org/10.3390/M65
Submission received: 27 February 1998 / Published: 6 March 1998
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Versions Notes
Molecules 03 m65 i001
The general part of the experimental section [1] has been presented elsewhere. To a stirred solution of (E)-2-methyl-5-phenyl-2-pentenoic acid (1.255 g, 6.6 mmol) in dry chloroform (15 ml) was added a solution of bromine (0.38 ml, 7.4 mmol) in dry chloroform (5 ml) dropwise. The mixture was stirred at room temperature for 6 hours and the chloroform solution was washed with sodium bisulfite solution (5%, 20 ml), brine (10 ml), dried (Na2SO4), filtered and evaporated under reduced pressure to yield 2,3-dibromo-2-methyl-5-phenyl-2-pentanoic acid (1.95 g, 84%) as yellow plates from chloroform/light petroleum.
M.p. 68-70° (resolidified and melted again at 86-8°)
Anal. calc. for C12H14Br2O2 (350.05): C 41.2, H 4.0; found: C 41.0, H 4.2.
IR (CDCl3) 3500-2800(bs, OH), 2954, 1722 (s, C=O), 1497, 1455, 1054 cm-1.
1H-NMR (400 MHz, CDCl3) 1.98 (3H, s, CH3), 2.04 (1H, m, 1/2 of CH2), 2.73 (2H, m, 1/2 of CH2 and 1/2 of Ph-CH2), 3.09 (1H, m, 1/2 of Ph-CH2), 4.56 (1H, m, -CHBr), 7.18-7.49 (5H, m, ArH), 8.10 (1H, bs, COOH).
13C-NMR (15 MHz, CDCl3 + DMSO-d6) 21.56 (CH3), 33.05, 34.35 (CH2), 58.31 (CHBr), 62.40 (C2), 125.5, 127.8, 127.8 (ArCH), 139.3 (quat, C1'), 169.7 (quat, C1).
EI-MS 352(M++4, 3%), 350(M++2, 6), 348 (M+, 3), 189(27), 143(41), 91(100), 65(19).
Acknowledgment: The authors gratefully acknowledge financial support from the Australian Research Council and The University of Sydney.

References and Notes

  1. Moloney, M.G.; Pinhey, J.T.; Stoermer, M.J. "Vinyl Cation Formation by Decomposition of Vinyl-lead Triacetates. The reactions of Vinylmercury and Vinyltin Compounds with Lead Tetraacetate". J. Chem. Soc. Perkin Trans. 1 1990, 10, 2645. [Google Scholar] [CrossRef]
Sample Availability: No sample available.

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MDPI and ACS Style

Stoermer, M.J.; Pinhey, J.T. 2,3-Dibromo-2-methyl-5-phenylpentanoic Acid. Molecules 1998, 3, M65. https://doi.org/10.3390/M65

AMA Style

Stoermer MJ, Pinhey JT. 2,3-Dibromo-2-methyl-5-phenylpentanoic Acid. Molecules. 1998; 3(3):M65. https://doi.org/10.3390/M65

Chicago/Turabian Style

Stoermer, Martin J., and John T. Pinhey. 1998. "2,3-Dibromo-2-methyl-5-phenylpentanoic Acid" Molecules 3, no. 3: M65. https://doi.org/10.3390/M65

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