2-Bromo-N-(4-fluorophenyl)-N-methylpropanamide synthesis
- Product Name:2-Bromo-N-(4-fluorophenyl)-N-methylpropanamide
- CAS Number:1283551-73-4
- Molecular formula:C10H11BrFNO
- Molecular Weight:260.1
Yield:1283551-73-4 88%
Reaction Conditions:
with potassium hydroxide in water;ethyl acetate at 4 - 11; for 1.5 h;
Steps:
2.5 4.2.5 2-Bromo-N-isopropyl-N-methylpropanamide (16)
General procedure: N-Isopropylmethylamine (1.0 mL, 9.8 mmol) was added to a biphasic solution of KOH (1.67 g, 29.7 mmol) in water (10 mL) and EtOAc (10 mL). This mixture was stirred rapidly and cooled to 4 °C whereupon 2-bromopropanoyl chloride (1.5 mL, 15 mmol) was added dropwise with the temperature kept below 11 °C. The ice bath was removed and stirring continued for 1.5 h. The organic phase was separated off and the aqueous phase extracted with EtOAc (5 mL x 2). The combined extracts were washed with brine (10 mL) and dried. The residue was distilled (bp 48-50 °C at 0.2 mmHg), but was still contaminated with 2-bromopropanoic acid. The oil was taken up in CHCl3 (10 mL), washed with NH4OH (5 mL x 3), water (5 mL), and brine (5 mL x 2), and then dried to give 16 as a colorless oil (588 mg, 29%).
References:
Brouwer, Chad;Jenko, Kimberly J.;Zoghbi, Sami S.;Morse, Cheryl L.;Innis, Robert B.;Pike, Victor W. [European Journal of Medicinal Chemistry,2016,vol. 124,p. 677 - 688]
