[C:1]([CH2:3][C:4]1[C:5]([F:21])=[C:6]([O:13]CC2C=CC=CC=2)[CH:7]=[CH:8][C:9]=1[N+:10]([O-])=O)#N.[C:22]([CH2:24][C:25]1[C:26]([N+:40]([O-])=O)=[CH:27][C:28]([F:39])=[C:29]([O:31]CC2C=CC=CC=2)[CH:30]=1)#N.[H][H]>C(O)C.C(O)(=O)C.[Pd]>[F:21][C:5]1[C:6]([OH:13])=[CH:7][CH:8]=[C:9]2[C:4]=1[CH:3]=[CH:1][NH:10]2.[F:39][C:28]1[CH:27]=[C:26]2[C:25]([CH:24]=[CH:22][NH:40]2)=[CH:30][C:29]=1[OH:31]A solution of a mixture of 3-cyanomethyl-2-fluoro-4-nitrobenzyloxybenzene and 5-cyanomethyl-2-fluoro-4-nitrobenzyloxybenzene (23 g, 80.4 mmol) in ethanol (220 ml) and acetic acid (30 ml) containing 10% palladium on charcoal (600 mg) was hydrogenated under 3 atmospheres pressure until hydrogen uptake ceased. The mixture was filtered and the filtrate was evaporated under vacuum. The residue was purified on column chromatography using a Prochrom® equipment eluting with methylene chloride/petroleum ether (20/80) to give 4-fluoro-5-hydroxyindole (2.48 g) and 6-fluoro-5-hydroxyindole (3.5 g).
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