Ethyl Bromide → 4-Ethoxy-2-fluoronitrobenzene
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].Br[CH2:13][CH3:14].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:13]([O:11][C:4]1[CH:5]=[CH:6][C:7]([N+:8]([O-:10])=[O:9])=[C:2]([F:1])[CH:3]=1)[CH3:14]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 3-fluoro-4-nitrophenol (1.57 g, 10.0 mmol) in 20 mL of dry DMF was added bromoethane (540 mg, 5.0 mmol) and K2CO3 powder (500 mg). The resulting reaction mixture was warmed to 50° C. and stirred for 1 h. It was quenched by addition of 20 mL of H2O, extracted with diethyl ether (100 mL×2). The combined organic extracts were washed with brine (50 mL), dried (MgSO4), filtered, and concentrated in vacuo to afford 4-ethoxy-2-fluoro-1-nitrobenzene as a pale yellow oil: MS (ESI) 186 (M+H)+.
Workup
- customThe resulting reaction mixture
- customIt was quenched by addition of 20 mL of H2O
- extractionextracted with diethyl ether (100 mL×2)
- washThe combined organic extracts were washed with brine (50 mL)
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-11fa4b8fa2484288ad3932fef51f4ca4
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07465730B2
Reaction notes
Loading…