Synthesis
General procedure for the synthesis of 4-fluoro-1,2-benzenediamine from 5-fluoro-2-nitroaniline: a methanol solution of 5-fluoro-2-nitroaniline (0.32 M) was added to a palladium/carbon catalyst (5% w/w, 10% w). The reaction mixture was stirred for 2 h at room temperature under hydrogen atmosphere (50 psi). Upon completion of the reaction, the mixture was filtered to remove the catalyst and the filtrate was concentrated to afford 4-fluoro-1,2-benzenediamine in 90% yield as a brown oil. Mass spectrometry (electrospray positive ion mode) analysis: the theoretical molecular weight of C6H7FN2 was 126 and the measured value was 127 (M + H)+.
References
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[3] Patent: WO2010/13037, 2010, A1. Location in patent: Page/Page column 67
[4] Synlett, 2018, vol. 29, # 13, p. 1765 - 1768
[5] Tetrahedron, 2017, vol. 73, # 27-28, p. 3898 - 3904
