9-Substituted phenanthrenes were used as target molecules in investigations of the effect of the reagent structure and reaction conditions on halogenation with bromine (1), ▫$CsSO_4F (2) and F-TEDA ...(1-chlormethyl-4-fluoro-1,4-diazoniabicycloe[2,2,2]octane bis(tetrafluoroborate), (3). 9-Methoxyphenanthrene (4) was converted to 9-bromo-10-methoxyphenantrene (4) was converted to 9-bromo-10-methoxyphenanthrene (6a) and 9-bromo-10-hydroxyphenanthrene (7a), while the amount of dealkylation depended on the solvent and was more pronounced in methanol than in acetonitrile, but no adduct was observed. Addition reaction became a major process in fluorination with CsSO_4F (2) in methanol and 88% of 9-fluoro-10,10-dimethoxy-9,10-hydrophenanthrene (8b) in methanol. Bromination of 9-hydroxyphenanthrene (5) in acetonitrile resulted only in the substitution process, while 9-fluoro-10-hydroxyphenenthrene (7b) formed in the reaction with CsSO_4F and F-TEDA was more reactive than the starting hydroxy derivative and using a 2 molar ratio of F-TEDA, only 9,9-difluoro-10-oxo-9,10-dihydrophenenthrene (9b) was formed.$▫
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