2-Methoxyethanol → 2-Fluoro-1-(2-methoxyethoxy)-4-nitrobenzene
Reaction equation
[CH3:1][O:2][CH2:3][CH2:4][OH:5].C([O-])([O-])=O.[K+].[K+].F[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][C:14]=1[F:22]>CN(C=O)C.O>[F:22][C:14]1[CH:15]=[C:16]([N+:19]([O-:21])=[O:20])[CH:17]=[CH:18][C:13]=1[O:5][CH2:4][CH2:3][O:2][CH3:1]Participants
6
Conditions
- Temperature
- 70 °C
Procedure
To a stirred suspension of methyl glycol (2.2 mL, 28.28 mmol, 1.5 eq.) and K2CO3 (7.8 g, 56.60 mmol, 3.0 eq.) in DMF (20 mL) was added 1,2-difluoro-4-nitrobenzene (3.0 g, 18.85 mmol, 1.0 eq.) and the mixture was stirred for 16 h at 70° C. The reaction mixture was cooled and diluted with water (30 mL) and extracted with ethyl acetate (40 mL). The organic layer was separated and washed with water (50 mL), brine (50 mL), and dried over sodium sulfate and the solvent evaporated under vacuum. The crude product was washed with n-pentane (30 mL) to obtain 2-fluoro-1-(2-methoxyethoxy)-4-nitrobenzene (3 g, 74%, as solid; TLC system: EtOAc/PE (1:9), Rf: 0.2).
Workup
- temperatureThe reaction mixture was cooled
- extractionextracted with ethyl acetate (40 mL)
- customThe organic layer was separated
- washwashed with water (50 mL), brine (50 mL)
- dry with materialdried over sodium sulfate
- customthe solvent evaporated under vacuum
- washThe crude product was washed with n-pentane (30 mL)
Sources & evidence
- ORD record
- ord-d5a4234134e841448a6f4a36a82ac52f
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946204B2
Reaction notes
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