Synthesis
General steps:
1. Thionyl chloride (4.00 mL, 52.2 mmol) was slowly added to a solution of 3-fluorophenylacetic acid (24.85 g, 158 mmol) in methanol (200 mL) at 0 °C.
2. The reaction mixture was stirred at room temperature for 3 hours and then concentrated under reduced pressure to remove the solvent.
3. The concentrated residue was extracted by partitioning between 1N sodium hydroxide solution (250mL) and ethyl acetate (250mL).
4. The organic layer was separated and washed with brine (100 mL) and subsequently dried over anhydrous magnesium sulfate.
5. The desiccant was removed by filtration and the filtrate was concentrated under reduced pressure to afford the colorless oily product methyl (3-fluorophenyl)acetate (25.81 g, 97% yield).
Product characterization data:
1H NMR (CDCl3) δ 3.62 (2H, s), 3.71 (3H, s), 6.92-7.09 (3H, m), 7.29 (1H, ddd, J = 7.9, 7.7, 6.0 Hz);.
IR (KBr) cm-1: 3065, 3024, 3001, 1955, 2845, 1740, 1616, 1593, 1489, 1450, 1437, 1342, 1258, 1200, 1165, 1144, 1076, 1015, 955, 930.
References
[1] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 13, p. 2843 - 2866
[2] Advanced Synthesis and Catalysis, 2012, vol. 354, # 4, p. 751 - 756
[3] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 14, p. 3719 - 3735
[4] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 15, p. 4694 - 4703
[5] Tetrahedron, 2002, vol. 58, # 51, p. 10113 - 10126
