Salicylaldehyde (98%, Sigma-Aldrich)
Ethyl Bromoacetate (98%, Sigma-Aldrich)
Potassium Carbonate (99.99%, trace metal basis, Sigma Aldrich)
Acetonitrile (ACS reagent, ≥99.5%, Sigma-Aldrich)

To a 1000 mL round bottom flask equipped with large stirbar was added salicylaldehyde (15.26 g, 125 mmol, 1 equiv), MeCN (830 mL, ≈ 0.15 M in the aldehyde), and K₂CO₃ (51.82 g, 375 mmol, 3 equiv). The solution rapidly became yellow and was stirred for five minutes. After this time, the α-bromo ester¹ (25.05 g, 150 mmol, 1.2 equiv) was added all at once, causing the solution to become colorless. The flask was then equipped with a reflux condenser and heated to reflux for 72 h while being vigorously stirred. After this time, the flask was cooled to room temperature and the solids were removed by filtration through a coarse² fritted funnel. The solids were washed thoroughly with Et₂O (250 mL) and the filtrate was transferred to a separatory funnel. Deionized water (≈ 500 mL) was added and the layers were separated. The aqueous layer was extracted with Et₂O (2 x 150 mL). The combine ether layers were washed with deionized water (2 x 200 mL), followed by brine (200 mL). The organic layer was dried with Na₂SO₄ and the solvent was removed³ in vacuo to give the desired ester (14.89 g, 63 %) as a clear yellow-orange oil.⁴

¹H NMR (CDCl₃, 400 MHz) d ppm 1.37 (t, J = 7.09 Hz, 3 H) 4.39 (q, J = 7.09 Hz, 2 H) 7.20 - 7.26 (m, 1 H) 7.37 (ddd, J = 8.44, 7.21, 1.22 Hz, 1 H) 7.46 (d, J = 0.98 Hz, 1 H) 7.53 (dd, J = 8.31, 0.73 Hz, 1 H) 7.58 - 7.63 (m, 1 H)

¹³C NMR (CDCl₃, 100 MHz) d ppm 14.37 (CH₃) 61.52 (CH₂) 112.36 (CH) 113.80 (CH) 122.85 (CH) 123.81 (CH) 127.03 (CH) 127.61 (C) 145.79 (C) 155.75 (C) 159.60 (C)

GC-MS (EI) 190 ([M]⁺, 68%) 162 (79%) 145 (100%) 134 (9%) 118 (42%) 89 (68%) 78 (8%) 63 (25%)

Korthals, K. A.; Wulff, W. D. J. Am. Chem. Soc., 2008, 130, 2898.