N-bromobutanimide → 4-Bromo-2-methoxy-6-methylaniline
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:4]=1[NH2:10].[Br:11]N1C(=O)CCC1=O>C(#N)C>[Br:11][C:7]1[CH:6]=[C:5]([CH3:9])[C:4]([NH2:10])=[C:3]([O:2][CH3:1])[CH:8]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 145 °C
Procedure
To 2-methoxy-6-methyl-phenylamine (10.0 g) dissolved in acetonitrile (200 mL) was added N-bromosuccinimide (14.3 g) and the reaction mixture was heated to 145° C. for 15 minutes in a sealed microwave process vessel. The crude mixture was filtered through Celite, diluted with diethyl ether (200 mL) and washed with sodium hydroxide (2 M, 2×100 mL) and brine (1×100 mL). The organic phase was dried over magnesium sulfate, concentrated in vacuo and purified by flash chromatography to furnish 3.4 g (26%) of the title compound as a black solid. 1H NMR (500 MHz, DMSO-d6): 2.06 (s, 3H), 3.77 (s, 3H), 4.55 (s, 2H), 6.78 (d, 1H), 6.82 (d, 1H).
Workup
- filtrationThe crude mixture was filtered through Celite
- additiondiluted with diethyl ether (200 mL)
- washwashed with sodium hydroxide (2 M, 2×100 mL) and brine (1×100 mL)
- dry with materialThe organic phase was dried over magnesium sulfate
- concentrationconcentrated in vacuo
- custompurified by flash chromatography
Sources & evidence
- ORD record
- ord-ec7bd3feee7c494c8bf862d38c986cb1
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07812023B2
Reaction notes
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