Synthesis
Example 10 Part A, Synthesis of 6-bromo-2,3-dihydro-1H-inden-1-ol: 6-bromo-1-indanone (1.4 g, 6.57 mmol) was dissolved in 20 mL of methanol, and sodium borohydride (0.087 g, 2.3 mmol) was slowly added over a period of 5 minutes at room temperature. The reaction mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, the mixture was concentrated under reduced pressure and then partitioned between ethyl acetate (50 mL) and 1N HCl (20 mL). The organic layer was separated, dried over sodium sulfate and subsequently concentrated under reduced pressure to afford the title compound 6-bromo-2,3-dihydro-1H-inden-1-ol as a solid (1.4 g, 99%). The product was characterized by 1H NMR (CDCl3): δ 7.45 (s, 1H), 7.3 (d, 1H), 7.0 (d, 1H), 5.2 (t, 1H), 2.9 (m, 1H), 2.7 (m, 1H), 2.4 (m, 1H), 1.9 (m, 2H).
References
[1] Patent: JP2016/29040, 2016, A. Location in patent: Paragraph 0058
[2] Patent: US2002/40022, 2002, A1
[3] Patent: WO2016/203401, 2016, A1. Location in patent: Page/Page column 58; 59; 60; 199
[4] Patent: WO2018/104766, 2018, A1. Location in patent: Page/Page column 58-60; 200-201
[5] Patent: WO2018/109648, 2018, A1. Location in patent: Page/Page column 83
