1,3-Dibromobenzene Explained

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.^[1]

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.^[2] 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.

See also

• 1,2-Dibromobenzene

Notes and References

1. Hartwell . Jonathan L. . o-Chlorobromobenzene . 1944 . 24 . 22 . . 10.15227/orgsyn.024.0022.
2. Early Clinical Development of Lufotrelvir as a Potential Therapy for COVID-19 . . 10.1021/acs.oprd.2c00375 . 3 February 2023 . 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 .