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1,3-Dibromobenzene
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M-Dibromobenzene.svg 100px 1,3-dibromobenzene 3d.png 150px 1,3-dibromobenzene sample.jpg 100px 1,3-Dibromobenzene m-Dibromobenzene 108-36-1 1904538 37151 13875356 203-574-2 363342 74EF6KH8TC 7927 1S/C6H4Br2/c7-5-2-1-3-6(8)4-5/h1-4H JSRLURSZEMLAFO-UHFFFAOYSA-N C1=CC(=CC(=C1)Br)Br
6 4 2 colorless liquidPubChem https://pubchem.ncbi.nlm.nih.gov/compound/7927 1,3-Dibromobenzene −7.0 218–220 1.9523 g/cm3 at 20.4 °C
1,2-Dibromobenzene 1,4-Dibromobenzene 1,3-Dichlorobenzene
1,3-Dibromobenzene (m-dibromobenzene) is an aryl bromide and isomer of dibromobenzene that is a colorless liquid at room temperature.
Preparation
1,3-Dibromobenzene may be prepared by diazotization of 3-bromoaniline, followed by a Sandmeyer reaction with cuprous bromide.Hartwell Jonathan L. o-Chlorobromobenzene 1944 24 22 Organic Syntheses 10.15227/orgsyn.024.0022 free
Uses
1,3-Dibromobenzene has been used as a starting material in the synthesis of antiviral Lufotrelvir, in human clinical trials for the treatment of COVID-19.Early Clinical Development of Lufotrelvir as a Potential Therapy for COVID-19 Organic Process Research & Development 10.1021/acs.oprd.2c00375 3 February 2023 27 12 2223–2239 Allais Christophe Bernhardson David Brown Adam R. Chinigo Gary M. Desrosiers Jean-Nicolas Dirico Kenneth J. Hotham Ian Jones Brian P. Kulkarni Samir A. Lewis Chad A. Lira Ricardo Loach Richard P. Morse Peter D. Mousseau James J. Perry Matthew A. Peng Zhihui Place David W. Rane Anil M. Samp Lacey Singer Robert A. Wang Zheng Weisenburger Gerald A. Yayla Hatice G. Zanghi Joseph M. 37552749 256584424 The first step is formylation of 1,3-dibromobenzene to 2,6-dibromobenzaldehyde, by lithiation with lithium diisopropylamide in THF, followed by quenching with dimethylformamide.
250px|Formylation of 1,3-dibromobenzene
See also
1,2-Dibromobenzene
1,4-Dibromobenzene
References
Category:Bromobenzenes