Grad Dip Arylpyrrole

2-bromo-2-methylpropionamide (97% yield) was synthesised from 2-bromoisobutyryl bromide.

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Synthesis of 2-bromo-2-methylpropionamide from 2-bromoisobutyryl bromide. To be used in investigating silver oxide coupling of tertiary alkylbromides with alcohols.

Reaction start time: 5:00 PM EST 24/6/13

2-bromoisobutyryl bromide (0.42 mL, 0.78 g, 0.39 mmol, 1 equiv.) was stirred in hexane (5 mL) at 0°C, to the mixture was added ammonium hydroxide (0.8 mL, 0.39 mmol, 1 equiv.) as 6 portions divided over 30 minutes. The reaction was stirred for another 30 minutes. A white percipitate formed, which was filtered and washed with cold water. A powdery white solid (0.34 g, 0.36 mmol, 97% yield).

Characterisation: ¹H-NMR(300MHz, CDCl₃): δ 1.97(s, 6H), 5.71(brs, 1H), 6.61(brs, 1H). M.P. of 150°C - 153°C, matched literature values.

NMR:

See also:

1. 2-bromo-2-methylpropionamide HNMR

Risk and Hazard Assessment:

Formation of methyl ester sulfonamide as a step towards forming 2-(1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-sulfonamido)acetate, a possible antimalarial.

Reaction start time: 2:00 PM EST 18/6/13

Risk and Hazard Assessment:

Same as second half of Synthesis of 2-(1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-sulfonamido)acetamide (MD 26-2)

Reaction start time: 11:00 AM EST, 17/6/13

Risk and Hazard Assessment:

Same as Chlorination of sodium 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-sulfonate using oxalyl chloride (MD 27-1)