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Short Note

2(S,R),3(R,S)-2,3-Dibromo-3-methyl-5-phenyl-2-pentanoic Acid

by
Martin J. Stoermer
2,* and
John T. Pinhey
1
1
Division of Organic Chemistry, School of Chemistry F11, The University of Sydney, N.S.W 2006, Australia
2
Current address: Victorian College of Pharmacy, Monash University (Parkville Campus), 381 Royal Parade, Parkville, Victoria 3052, Australia
*
Author to whom correspondence should be addressed.
Molecules 1998, 3(3), M55; https://doi.org/10.3390/M55
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 m55 i001
The general part of the experimental section [1] has been presented elsewhere. To a stirred solution of (E)-3-methyl-5-phenyl-2-pentenoic acid (2.26 g, 12 mmol) in dry chloroform (50 ml) was added a solution of bromine (0.75 ml, 15 mmol) in dry chloroform (5 ml) dropwise. The mixture was stirred at room temperature for 16 hours and evaporated under reduced pressure to yield 2(S,R),3(R,S)-2,3-dibromo-3-methyl-5-phenyl-2-pentenoic acid (4.18 g, 100%) as yellow plates from chloroform/light petroleum.
M.p. 115-8°
UV (ethanol) 206 (11360) nm.
IR (CDCl3) 3260-2758(bs, OH), 1728 (s, C=O) cm-1.
1H-NMR (90 MHz, CDCl3) 2.03-2.40 (2H, m, CH2), 2.06 (3H, s, CH3), 2.70-3.03 (2H, m, CH2), 4.66 (1H, s, -CHBr), 7.02-7.40 (5H, m, ArH), 10.22 (1H, bs, COOH).
13C-NMR (15 MHz, CDCl3) 26.75 (CH3), 31.88, 45.91 (CH2), 51.75 (CHBr), 65.77 (C3), 126.3, 128.5
128.6 (ArCH), 140.5 (quat, C1'), 172.2 (quat, C1).
EI-MS 352(M++4, 3%), 350(M++2, 6), 348 (M+, 4), 146(40), 145(68), 143(36), 131(40), 129(36), 128(37), 115(30), 105(30), 103(30), 92(49), 91(100).

Supplementary Materials

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(S,R),3(R,S)-2,3-Dibromo-3-methyl-5-phenyl-2-pentanoic Acid. Molecules 1998, 3, M55. https://doi.org/10.3390/M55

AMA Style

Stoermer MJ, Pinhey JT. 2(S,R),3(R,S)-2,3-Dibromo-3-methyl-5-phenyl-2-pentanoic Acid. Molecules. 1998; 3(3):M55. https://doi.org/10.3390/M55

Chicago/Turabian Style

Stoermer, Martin J., and John T. Pinhey. 1998. "2(S,R),3(R,S)-2,3-Dibromo-3-methyl-5-phenyl-2-pentanoic Acid" Molecules 3, no. 3: M55. https://doi.org/10.3390/M55

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