Dichloromethane → 2-fluoro-4-nitro-N,N-bis(2-propoxyethyl)aniline
Reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[F:11].CCN(CC)CC.[CH2:19]([O:22][CH2:23][CH2:24][NH:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][CH3:31])[CH2:20][CH3:21].C(Cl)Cl>CN(C=O)C>[F:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[N:25]([CH2:26][CH2:27][O:28][CH2:29][CH2:30][CH3:31])[CH2:24][CH2:23][O:22][CH2:19][CH2:20][CH3:21]Participants
6
Conditions
- Temperature
- 90 °C
Procedure
To a solution of 1,2-difluoro-4-nitrobenzene (2.94 g, 18.45 mmol) in DMF (30 mL) were added Et3N (3.11 g, 30.75 mmol) and bis(2-propoxyethyl)amine (1.16 g, 6.15 mmol) with stirring. The reaction mixture was heated at 90° C. overnight, then cooled to rt and poured into CH2Cl2 (100 mL). The organic phase was washed with water (100 mL×3), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=10:1) to give the title compound as yellow oil (1.47 g, 73%).
Workup
- temperaturecooled to rt
- washThe organic phase was washed with water (100 mL×3)
- dry with materialdried over anhydrous Na2SO4
- concentrationconcentrated in vacuo
- customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=10:1)
Sources & evidence
- ORD record
- ord-db51c45263e2407587b96fb45ea2c8f1
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434695B2
Reaction notes
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