1-Bromo-4-iodobenzene → 4-Bromo-N-ethyl-N-methylaniline
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.[CH3:9][NH:10][CH2:11][CH3:12].C1C=C2C=CC(O)=C(C3C4C(=CC=CC=4)C=CC=3O)C2=CC=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu]Br.CN(C)C=O>[CH2:11]([N:10]([CH3:9])[C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)[CH3:12]Participants
Conditions
- Temperature
- 70 °C
Procedure
A mixture of 1-bromo-4-iodobenzene (2.0 g, 7.07 mmol), N-methylethylamine (3.0 ml, 35.3 mmol), copper(I) bromide (203 mg, 1.41 mmol), 1,1′-bi-2-naphthol (405 mg, 1.41 mmol), tripotassium phosphate (3.0 g, 14.1 mmol) and anhydrous N,N-dimethylformamide (20 ml) was stirred at 70° C. for 2 days. After cooling to room temperature, the mixture was filtered through a Celite pad, and the insoluble material was washed with ethyl acetate. The filtrate and washing solution were combined and washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100→2:98) to give N-ethyl-4-bromo-N-methylaniline (1.04 g, yield 69%) as a yellow oil.
Workup
- temperatureAfter cooling to room temperature
- filtrationthe mixture was filtered through a Celite pad
- washthe insoluble material was washed with ethyl acetate
- washThe filtrate and washing solution
- washwashed with water
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100→2:98)
Sources & evidence
- ORD record
- ord-c2cb6c943c0c41b4ab5e69a44cbc18fa
- Source dataset
- uspto-grants-2015_04
- Patent number
- US08999989B2
Reaction notes
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