Isopropanol → 4-Chloro-alpha-(2-fluorophenyl)benzenemethanol
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])=[O:9])=[CH:4][CH:3]=1.CC(O)C.[BH4-].[Na+]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])[OH:9])=[CH:6][CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a stirred and refluxing mixture of 23.4 parts of (4-chlorophenyl) (2-fluorophenyl)methanone in 280 parts of 2-propanol are added portionwise 3.7 parts of sodium borohydride. Upon completion, stirring is continued for 2 hours at reflux temperature (±80° C.). The reaction mixture is cooled and decomposed by the addition of water. The 2-propanol is evaporated and the residual product is extracted with trichloromethane. The extract is dried, filtered and evaporated, yielding 4-chloro-α-(2-fluorophenyl)benzenemethanol as a residue.
Workup
- temperaturerefluxing
- stirringUpon completion, stirring
- temperatureThe reaction mixture is cooled
- customThe 2-propanol is evaporated
- extractionthe residual product is extracted with trichloromethane
- customThe extract is dried
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-12a6cb03240a438985a160118d4a5515
- Source dataset
- uspto-grants-1983_03
- Patent number
- US04377578
Reaction notes
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