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

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), M56; https://doi.org/10.3390/M56
Submission received: 27 February 1998 / Published: 6 March 1998
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Molecules 03 m56 i001
The general part of the experimental section [1] has been presented elsewhere. To a stirred solution of (Z)-3-methyl-5-phenyl-2-pentenoic acid (0.575 g, 3 mmol) in dry chloroform (10 ml) was added a solution of bromine (0.2 ml, 4 mmol) in dry chloroform (3 ml) dropwise. The mixture was stirred at room temperature for 16 hours and evaporated under reduced pressure to yield 2(R,S),3(S,R)-2,3-dibromo-3-methyl-5-phenyl-2-pentenoic acid (1.05 g, 99%) as an orange solid.
M.p. 115-8°
UV (ethanol) 206 (11390) nm.
IR (CDCl3) 3300-2800(bs, OH), 1723 (s, C=O) cm-1.
1H-NMR (90 MHz, CDCl3) 1.81-3.14 (4H, m, 2xCH2), 1.96 (3H, s, CH3), 4.69 (1H, s, -CHBr), 6.96-7.44 (5H, m, ArH), 9.68 (1H, bs, COOH).
13C-NMR (15 MHz, CDCl3) 29.67 (CH3), 32.40, 41.36 (CH2), 54.93 (CHBr), 66.36 (C3), 126.1, 128.4,
128.4 (ArCH), 140.6 (quat, C1'), 172.3 (quat, C1).
EI-MS 352(M++4, 1%), 350(M++2, 2), 348 (M+, 2), 146(17), 145(67), 143(27), 131(28), 129(35),
128(23), 115(16), 105(16), 103(13), 92(49), 91(100).

Supplementary Materials

Acknowledgments

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(R,S),3(S,R)-2,3-Dibromo-3-methyl-5-phenyl-2-pentanoic Acid. Molecules 1998, 3, M56. https://doi.org/10.3390/M56

AMA Style

Stoermer MJ, Pinhey JT. 2(R,S),3(S,R)-2,3-Dibromo-3-methyl-5-phenyl-2-pentanoic Acid. Molecules. 1998; 3(3):M56. https://doi.org/10.3390/M56

Chicago/Turabian Style

Stoermer, Martin J., and John T. Pinhey. 1998. "2(R,S),3(S,R)-2,3-Dibromo-3-methyl-5-phenyl-2-pentanoic Acid" Molecules 3, no. 3: M56. https://doi.org/10.3390/M56

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