Sodium borohydride → Anisole
Reaction equation
[BH4-].[Na+].[Br:3][C:4]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:5]=1[CH:6]([OH:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Br[C:20]1[CH:33]=[C:32]2[O:34][CH2:35]O[C:31]2=[CH:30][C:21]=1[CH:22]([OH:29])C1C=CC=CC=1.[Br:37][C:38]1[CH:51]=[C:50](OC)[C:49](OC)=[CH:48][C:39]=1[CH:40]([OH:47])C1C=CC=CC=1>>[C:32]1([O:34][CH3:35])[CH:33]=[CH:20][CH:21]=[CH:30][CH:31]=1.[Br:37][C:38]1[CH:51]=[CH:50][CH:49]=[CH:48][C:39]=1[C:40]([Cl:18])=[O:47].[Br:3][C:4]1[CH:17]=[CH:16][CH:15]=[CH:14][C:5]=1[C:6]([C:7]1[CH:12]=[CH:11][C:10]([O:29][CH3:22])=[CH:9][CH:8]=1)=[O:13]Participants
Procedure
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.
Sources & evidence
- ORD record
- ord-004dea035dbd46e2b459cb91efc21cc0
- Source dataset
- uspto-grants-1976_05
- Patent number
- US03959475
Reaction notes
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