Dimethylformamide → 4-Bromo-2-chloro-N,N-dimethylaniline

HRID 1839944Notes

Reaction equation

IC.[Br:3][C:4]1[CH:10]=[CH:9]C(N)=[C:6]([Cl:11])[CH:5]=1.C([O-])([O-])=O.[K+].[K+].[CH3:18][N:19]([CH:21]=O)[CH3:20]>>[Br:3][C:4]1[CH:10]=[CH:9][C:21]([N:19]([CH3:20])[CH3:18])=[C:6]([Cl:11])[CH:5]=1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 6328Methyl iodide

HCID 11430Potassium Carbonate

HCID 6101694-Bromo-2-chloroaniline

Product 1

HCID 126372844-Bromo-2-chloro-N,N-dimethylanilineYield 78%

Procedure

Under nitrogen, 11.6 mL (186 mmol) of iodomethane was added to a stirred solution of 12.8 g (62 mmol) of 4-bromo-2-chloroaniline and 42.8 g (310 mmol) of powdered K2CO3 in 200 mL of DMF. Purification by silica gel chromatography (Waters Prep-500A) with ethyl acetate/hexane (5:95) gave 11.3 g (78%) of 4-bromo-2-chloro-N,N-dimethylaniline as a colorless liquid: NMR (CDCl3) δ 2.79 (s, 6H), 6.92 (d, J=9 Hz, 1H), 7.25-7.34 (m, 1H), 7.49 (d, J=2 Hz, 1H)

Workup

customPurification by silica gel chromatography (Waters Prep-500A) with ethyl acetate/hexane (5:95)

Sources & evidence

ORD record: ord-074f954cbae74142a069a9e05fdfe823
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06677488B2

Reaction notes

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