Ethyl oxoacetate → 7-Bromo-3-methylnaphthalen-1-ol

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반응 단계

7-Bromo-3-methylnaphthalen-1-ol was prepared in a similar manner as 6-chloro-3-methylnaphthalen-1-ol in Example 5 except using 1-(4-bromophenyl)propan-2-one instead of 1-(3-chlorophenyl)propan-2-one. To a solution of 7-bromo-3-methylnaphthalen-1-ol (11.5 g, 48.5 mmol) in dichloromethane (145 mL) at 0° C. was added a 1 M titanium(IV) chloride solution in dichloromethane (48.5 mL, 48.5 mmol) and stirred for 20 min. Ethyl glyoxylate (50% solution in PhCH3, 10.6 mL, 53.3 mmol) was added over 15 minutes and stirred for 1 hour at 0° C. The reaction was quenched by the addition of Rochelle's salt solution and stirred at room temperature for 14 hours. The layers were separated, and the aqueous layer was extracted with CH2Cl2. The combined organic layers were dried, filtered, concentrated and purified by flash column chromatography (EtOAc/Hexanes) to provide the desired product. 1H-NMR: 400 MHz, (CDCl3) δ: 8.52 (s, 1H), 8.34 (s, 1H), 7.49 (m, 2H), 7.13 (s, 1H), 5.67 (s, 1H), 4.24 (m, 1H), 4.16 (m, 1H), 2.29 (s, 3H), 1.23 (m, 3H).

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