Preparation of N,N-dimethylation of 4-bromoaniline?

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Frank T. Edelmann

Dear Anees Ahmad, attached are two varieties of the methylation of 4-bromoaniline using MeI. Apparently the reaction doesn't work with methyl iodide alone. Both methods require the presence of a base.

Adel Amer

Ahmad

You may use the following procedure which gives 99% yield

Add sodium cyanoborohydride (1.13 g, 17.98 mmol, 2.0 equivalents) to a stirred slurry of p-bromoaniline (1.559 g) and paraformaldehyde (18.6 mmol) in glacial acetic acid (15 mL) at 0 °C.

Stir the resultant mixture at 0 °C for 25 minutes.

Remove the ice bath.

Heat the mixture to 65 °C (external oil bath temperature).

Stir the mixture at 65 °C for 3 hours.

Pour the hot reaction mixture over 5M aqueous sodium hydroxide solution (60 mL, 300 mmol, 1.1 equivalents to acetic acid).

Dilute the hot reaction mixture with ethyl acetate (30 mL).

Separate the layers.

Extract the aqueous layer with ethyl acetate (2 × 20 mL).

Wash the combined organic layers sequentially with water (20 mL) and saturated aqueous sodium chloride solution (20 mL).

Dry the combined organic layers over anhydrous sodium sulfate.

Filter the dried solution.

Concentrate the solution. from Bush, Timothy S. et al Organic Letters, 20(17), 5406-5409; 2018

You may also try this (90% yield)

Add glacial acetic acid (7.3 mL, 130 mmol, 5.4 equivalents) dropwise to a mixture of 4-bromoaniline (3.0 g), paraformaldehyde (3.9 g) and sodium cyanoborohydride (7.9 g, 130 mmol, 5.4 equivalents) in tetrahydrofuran (100 mL) at 23 °C.

Heat the resultant mixture to 50 °C.

Stir the resultant mixture at 50 °C for 18 hours.

Cool the reaction mixture to 23 °C.

Partition the reaction mixture between saturated aqueous sodium bicarbonate solution (100 mL) and diethyl ether (40 mL).

Extract the aqueous layer with diethyl ether (2 × 40 mL).

Wash the combined organic layers sequentially with water (2 × 60 mL) and saturated aqueous sodium chloride solution (3 × 40 mL).

Concentrate the dried solution.

Purify the resultant residue by flash column chromatography (silica gel, starting with 5% ethyl acetate-hexane, grading to 10% ethyl acetate-hexane). From Reed, Hayley et al Journal of Organic Chemistry, 83(18), 11359-11368; 2018 Good Luck

Madhukar Baburao Deshmukh

N,N-dimethyl 4-bromoaniline is obtained by heating 1 mole of 4-bromo aniline with 2-moles of methyl chloride or dimethyl sulphate.followed by the neutralization with aque. NaOH.