Dimethylformamide → (S)-2-(4-bromo-2-nitrophenylamino)propan-1-ol
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](F)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.CN(C=O)C.C(=O)([O-])[O-].[K+].[K+].[NH2:23][C@@H:24]([CH3:27])[CH2:25][OH:26]>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:23][C@@H:24]([CH3:27])[CH2:25][OH:26])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1Participants
Conditions
- Temperature
- 60 °C
Procedure
A 1-L, three-necked, round bottomed flask fitted with a nitrogen inlet, overhead stirrer, thermocouple, and condenser was charged with 4-bromo-1-fluoro-2-nitrobenzene (46 g, 209 mmol), DMF (230 mL), potassium carbonate (31.8 g, 230 mmol), and (S)-2-aminopropane-1-ol (17.9 mL, 230 mmol). The reaction mixture was heated to 60° C. for 6 h and then cooled to rt and stirred overnight. The mixture was slowly diluted with water (690 mL), and the resulting slurry stirred at rt for 3 h and was then filtered. The solids were washed with water (120 mL) and dried under house vacuum (ca 17 Torr) overnight to afford (S)-2-(4-bromo-2-nitrophenylamino)propane-1-ol (72.98 g) as a yellow-orange solid which contained excess water, and was used in next step without further drying or purification. MS (ESI, pos. ion) m/z 275 [M+1]+.
Workup
- temperaturecooled to rt
- stirringthe resulting slurry stirred at rt for 3 h
- filtrationwas then filtered
- washThe solids were washed with water (120 mL)
- customdried under house vacuum (ca 17 Torr) overnight
Sources & evidence
- ORD record
- ord-6b1e0a4c349d46a2ac4c377ffd910b2c
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09422281B2
Reaction notes
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