4-Fluorobiphenyl → Eisessig-Jodwasserstoff
Reaction equation
FC1C=CC(C2C=CC(C(C)CCC(N)=O)=CC=2)=CC=1.[F:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:24][CH:23]=1.C1(=O)[O:39][C:37](=[O:38])[CH2:36]C1.[Al+3].[Cl-].[Cl-].[Cl-].FC1C=CC(C2C=C[C:55]([C:58](=[O:64])[CH2:59][CH2:60][C:61]([OH:63])=[O:62])=CC=2)=CC=1.C[Mg][I:67]>>[F:21][C:22]1[CH:23]=[CH:24][C:25]([C:28]2[CH:33]=[CH:32][C:31]([C:58]([OH:64])([CH3:55])[CH2:59][CH2:60][C:61]([OH:63])=[O:62])=[CH:30][CH:29]=2)=[CH:26][CH:27]=1.[IH:67].[C:37]([OH:39])(=[O:38])[CH3:36]Participants
Reactant 5
Product 2
Procedure
A 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°.
Workup
- customto give
Sources & evidence
- ORD record
- ord-de2aec64f9f64ffea189668cf5c62cd5
- Source dataset
- uspto-grants-1978_08
- Patent number
- US04110447
Reaction notes
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