Dimethyl Sulfoxide → 5-Bromo-2-morpholinonitrobenzene
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.CS(C)=O.[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1Participants
4
Procedure
To a solution of 4-bromo-1-fluoro-2-nitrobenzene (10.088 g, 45.9 mmol) in dimethyl sulfoxide (20.00 mL, 282 mmol) was added morpholine (6.00 mL, 68.8 mmol). A vigorous exotherm developed and the solution turned an intense orange-red. After 10 min LC-MS indicated no starting material remained and the desired product predominated. The reaction was poured into 200 mL satd aq. Sodium bicarbonate solution and the aq. Mixture was extracted with 200 mL Et2O. The ether extract was washed with 100 mL water followed by 100 mL brine then stirred over anhydrous magnesium sulfate, filtered and the filtrate concd under reduced pressure to afford an orange oil. Mass Spectrum (ESI) m/e=287.0 & 289.0 (M+1).
Sources & evidence
- ORD record
- ord-d1f82d9a85144ec4a3384ccc953020f6
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08940724B2
Reaction notes
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