O=S(Cl)[Cl:3].N.BrBr.[F:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([CH:21]([CH3:27])[CH2:22][CH2:23][N:24]=C=O)=[CH:17][CH:16]=2)=[CH:11][CH:10]=1>O1CCOCC1.[OH-].[K+].CCOCC.O.CO>[ClH:3].[F:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([CH:21]([CH3:27])[CH2:22][CH2:23][NH2:24])=[CH:17][CH:16]=2)=[CH:13][CH:14]=1A solution of 27.1 g of 4-(4'-fluoro-4-biphenylyl)pentanoic acid amide [obtainable by reacting 4-fluorobiphenyl with succinic anhydride/AlCl3 to give 4-(4'-fluoro-4-biphenylyl)-4-oxobutanoic acid, reaction with CH3MgI to give 4-(4'-fluoro-4-biphenylyl)-4-hydroxy-pentanoic acid, dehydroxylation with HI/acetic acid to give 4-(4'-fluoro-4-biphenylyl)-pentanoic acid, conversion into the chloride employing SOCl2 and reaction with NH3 ] in 150 ml of dioxane is added dropwise at 0° to a solution of 24 g of bromine in 120 ml of 20% potassium hydroxide solution. The mixture is stirred for a further 1 hour, taken up in ether, the phases are separated and the organic phase is dried over sodium sulfate and evaporated. The crude product obtained is boiled for 20 hours with 60 g of KOH, 250 ml of methanol and 65 ml of water, in the course of which 3-(4' -fluoro-4-biphenylyl)-butyl-isocyanate, which is not isolated, is formed. After cooling, the mixture is worked up using water and ether to give 3-(4'-fluoro-4-biphenylyl)-butylamine, hydrochloride; m.p. 222°-224°.
Wird geladen…
