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borane; hydrochlorid acid; tetrahydrofuran; 1,4-dioxane; ethyl acetate;

reactants are commercially availlable.
miao, hua, wo2015/89337, a1, (2015) [0617j to a solution of 4-bromo-2-methylbenzonitrile (3.0 g, 15 mmol) in anhydrous thf (20 ml) under nitrogen at 0 °c was added 1.0 m solution of borane in thf (46 ml). the reaction mixture was stirre d at 0 °c for 1 h, and heated at 80 °c overnight. the reaction mixture was cooled to 0 °c and slowly quenched with meoh, concentrated in vacuo. the crude product was treated with etoac (20 ml) and 4 m of hc1 in 1,4-dioxane (8.0 ml, 32 mmol) for 5 mm. the solid was filtered, rinsed with diethyl ether, dried to give the title compound as a white powder (3.24 g, yield: 100percent). lcms: rt 0.75 mm.; mh 200.0. ?h nmr (300 mhz, dmsod6) 5: 8.28 (br. s., 2h), 7.42 - 7.54 (m, 2h), 7.34 (d, j = 7.93 hz, 1h), 3.99 (d, j = 4.15 hz, 2h), 2.35 (s, 3h).

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