Hydrochloric Acid → 3-Fluoro-4-nitrobenzyl alcohol
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5](O)=[O:6].Cl>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 3-fluoro-4-nitrobenzoic acid (2.0 g, 10.8 mmol) in THF (50 ml) at 0° C. was added BH3.Me2S complex (2.215 ml, 22.15 mmol) drop-wise. The mixture was stirred at 0° C. for 3 h, and was then stirred at 65° C. for 18 h. To the cooled mixture was added ice (50 g), followed by 1 N aq. HCl (100 ml), and the resulting mixture was extracted with EtOAc (200 ml). The organic layer was dried over Na2SO4, filtered and concentrated in vacuo to provide the title compound as a white solid (1.79 g, 97%).
Workup
- stirringwas then stirred at 65° C. for 18 h
- extractionthe resulting mixture was extracted with EtOAc (200 ml)
- dry with materialThe organic layer was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-973d2c5a10ab4047acd96d5dc5766260
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08986740B2
Reaction notes
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