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Typical Procedure: A dry and argon filled 25 mL flask, equipped with a magnetic stirrer and a septum, was charged with a solution of 1,5-bis(bromomagnesium)pentane (0.46 M/THF, 4.4 mL, 2.0 mmol) in THF (8 mL). The solution of CuCN·2LiCl in THF (1.0 M/THF, 2.0 mL, 2.0 mmol) was added dropwise at -78 °C. The resulting mixture was stirred for 30 min and ethyl 4-iodobenzoate 4a (552 mg, 2.0 mmol) was added at -78 °C. The resulting mixture was warmed to r.t. for 1 h and then benzoyl chloride (421 mg, 3.0 mmol) was added. After 30 min, the solution was quenched with sat. aq NH4Cl solution and poured into H2O (20 mL). The organic layer was separated and the aqueous phase was extracted with Et2O (3 × 50 mL). The organic fractions were washed with brine (30 mL), dried over MgSO4 and concentrated in vacuo. Purification by chromatography (SiO2, n-pentane/Et2O = 50:1) yielded 478 mg (94% yield) of 8b as a colorless oil. IR (film): 3402 (m, br), 2982 (m), 1720(vs), 1661 (vs), 1597 (m), 1579 (w), 1448 (m), 1405 (s), 1356 (s), 1369 (s), 1317 (s), 1275(vs), 1105(vs), 1020 (m), 939 (m), 927 (m), 851 (w), 769 (w), 715 (s), 698 (m), 657 (m)cm-1. 1H NMR (300 MHz, CDCl3): δ = 8.07 (dd, J = 8.4 and 1.8 Hz, 2 H), 7.73 (m, 4 H), 7.53 (m, 1 H), 7.40 (t, J = 8.0 Hz, 2 H), 4.34 (q, J = 7.2 Hz, 2 H), 1.33 (t, J = 7.1 Hz, 3 H). 13C NMR (75 MHz, CDCl3): δ = 195.0, 164.8, 140.2, 136.0, 132.6, 131.9, 129.1, 128.7, 128.4, 127.4, 126.2, 60.4, 13.3. MS (EI, 70 eV): m/z (%) = 254 (48) [M+], 226 (14), 209 (45), 181 (18), 177 (57), 152 (10), 149 (14), 130 (20), 118 (17), 104 (100). HRMS (EI): calcd for C16H14O3 [M+]: 527.7580. Found: 527.7579.