Potassium Carbonate → 2-Fluoro-4-(4-methoxybenzyloxy)-1-nitrobenzene
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].Cl[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([O:11][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]Participants
6
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 3-fluoro-4-nitrophenol (2.96 g, 18.81 mmol) in DMF (18.81 mL) was added 1-(chloromethyl)-4-methoxybenzene (2.55 mL, 18.81 mmol) and potassium carbonate (5.20 g, 37.6 mmol). The reaction mixture was stirred at 50° C. for 16 hours. The mixture was diluted with EtOAc (100 mL), washed with water, and the aqueous layer was back-extracted with EtOAc (25 mL). The combined organic layers were washed with 1 M aqueous NaOH (20 mL) and then with brine. The organic layer was dried over Na2SO4, filtered and evaporated. The yellow solid was triturated with ether (20 mL), and the solid was collected, rinsing with ether (5 mL). The title compound was obtained as a yellow solid (4.39 g, 84% yield).
Workup
- washwashed with water
- extractionthe aqueous layer was back-extracted with EtOAc (25 mL)
- washThe combined organic layers were washed with 1 M aqueous NaOH (20 mL)
- dry with materialThe organic layer was dried over Na2SO4
- filtrationfiltered
- customevaporated
- customThe yellow solid was triturated with ether (20 mL)
- customthe solid was collected
- washrinsing with ether (5 mL)
Sources & evidence
- ORD record
- ord-2ce96882ba7f48739399664c791b5c9b
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09115127B2
Reaction notes
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