Reaktionsgleichung
[Br:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[CH:4]([OH:13])[C:5]1[CH:10]=[CH:9][C:8](OC)=[CH:7][CH:6]=1.Br[C:19]1C=C(C)C=CC=1C=O.C1([Mg]Br)C=CC=CC=1>>[Br:1][C:2]1[CH:17]=[C:16]([CH3:19])[CH:15]=[CH:14][C:3]=1[CH:4]([OH:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1Komponenten
Versuchsvorschrift
Friedel-Crafts acylation of m-bromoanisole with benzoyl chloride and p-fluorobenzoyl chloride provides 2-bromo-4-methoxybenzophenone, m.p. 83°-84°, and 2-bromo-4'-fluoro-4-methoxybenzophenone, m.p. 79°-81°, respectively, which are reduced with sodium borohydride to 2-bromo-4-methoxybenzhydrol, b.p. 160° (0.05 mm.), and 2-bromo-4'-fluoro-4-methoxybenzhydrol, a liquid. Acylation of benzene with 2-bromo-5-chlorobenzoyl chloride, 2-bromo-4,5-methylene dioxybenzoyl chloride, and 2-bromo-4,5-dimethoxybenzoyl chloride provides 2-bromo-5-chlorobenzophenone, 2-bromo-4,5-methylene-dioxybenzophenone, and 2-bromo-4,5-dimethoxybenzophenone, m.p. 76°-77°, which are reduced with sodium borohydride to 2-bromo-5-chlorobenzhydrol, 2-bromo-4,5-methylenedioxybenzhydrol, and 2-bromo-4,5dimethoxybenzhydrol, m.p. 83°-85°. Acylation of anisole with 2-bromobenzoyl chloride provides 2-bromo-4'-methoxybenzophenone, m.p. 93°-95°, which is reduced to 2-bromo-4'-methoxybenzhydrol, m.p. 64°-65°. Reaction of 2-bromo-4-methylbenzaldehyde and phenylmagnesium bromide provides 2-bromo-4-methylbenzhydrol.
Quellen und Nachweise
- ORD-Eintrag
- ord-1983cbadfeba4ababefab08526b4d977
- Quelldatensatz
- uspto-grants-1976_05
- Patentnummer
- US03959475
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