Methanol → (2-Fluoro-3-nitrophenyl)methanol
Reaction equation
CC(C[AlH]CC(C)C)C.C[O:11][C:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[C:14]=1[F:22].CO.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[F:22][C:14]1[C:15]([N+:19]([O-:21])=[O:20])=[CH:16][CH:17]=[CH:18][C:13]=1[CH2:12][OH:11]Participants
7
Conditions
- Temperature
- 0 °C
Procedure
DIBAL (115.7 mL, 1.0 M in toluene) was added at −78° C. to a solution of 2-fluoro-3-nitrobenzoic acid methyl ester (compound 2b-1) (9.22 g, 46.3 mmol) in toluene (92 mL), and the reaction mixture was stirred at −78° C. for 30 minutes and at 0° C. for 30 minutes. The resultant reaction solution was cooled again to −78° C., and methanol, aqueous saturated Rochelle salt solution and ethyl acetate were added thereto. The reaction mixture was then stirred at room temperature for 1 hour, and extracted three times with ethyl acetate. The organic layer was washed with saturated saline and dried over magnesium sulfate. The title compound (7.52 g, 95%) was then obtained by vacuum concentration as a brown oil.
Workup
- customThe resultant reaction solution
- temperaturewas cooled again to −78° C.
- stirringThe reaction mixture was then stirred at room temperature for 1 hour
- extractionextracted three times with ethyl acetate
- washThe organic layer was washed with saturated saline
- dry with materialdried over magnesium sulfate
Sources & evidence
- ORD record
- ord-843bab93a7f94a7ba27edd71ee8cc18c
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08569378B2
Reaction notes
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