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With sodium tetrahydroborate In methanol at -10℃; for 0.166667 h;
[Step 2] Synthesis of (4-bromo-2-(trifluoromethoxy)phenyl)methanol: At -10°C, sodium borohydride (2.4 g, 63 mmol) was added to a solution of Reference Example Compound 1 (16 g, 59 mmol) in methanol (0.23 L). After stirring the resulting reaction solution at -10°C for 10 minutes, acetone (10 mL) and 1 N hydrochloric acid (10 mL) were added thereto. The reaction solution was then concentrated under reduced pressure, and water was added to the obtained crude product, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (eluent, hexane:ethyl acetate = 50:1 → 1:1) to obtain 15 g (91percent) of (4-bromo-2-(trifluoromethoxy)phenyl)methanol (hereinafter referred to as Reference Example Compound 2).
Reference：
[1] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 9, p. 1311 - 1316
[2] Patent: EP2832724, 2015, A1, . Location in patent: Paragraph 0124
[3] Patent: US5968938, 1999, A,
[4] Patent: US6090805, 2000, A,
[5] Patent: WO2010/96722, 2010, A1, . Location in patent: Page/Page column 60-62
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