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Intermediate 10) Synthesis of 5-(4-(methylsulfonyI)tetrahydro-2jfiT-pyran-4- yI)benzo [b] thiophene-2-carboxylic acid (a) Synthesis of 4-(4-fluoro-3-methylphenyl)tetrahydro-2H-pyran-4-ol 4-Bromo-l-fluoro-2-methylbenzene (1.0 g, 5.29 mmol) was dissolved in anhydrous THF (26.0 mL), and 1.6M solution of -BuLi in THF (3.5 mL, 5.55 mmol) and tetrahydro-4H-pyran-4-one (556.0 mg, 5.55 mmol) were added at -78C. The reaction mixture was stirred at 0C for 2 hours, H20 was added, and extracted with EtOAc. The organic extract was washed with brine, dried over anhydrous Na2S04 and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, n-Hex : EtOAc = 1 : 1) to obtain 4-(4-fluoro-3-methylphenyl)tetrahydro-2H- pyran-4-ol (800.0 mg, 72%) as a white solid. 1H-NMR (400MHz, CDC13): delta 7.31 (dd, 1H, J=7.3, 2.2Hz), 7.26 (m, 1H), 6.99 (t, 1H, J=8.9Hz), 3.84-3.98 (m, 4H), 2.29 (s, 3H), 2.08-2.18 (m, 2H), 1.65-1.69 (m, 3H)

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-Bromo-1-fluoro-2-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; C&C RESEARCH LABORATORIES; PARK, Chan Hee; LEE, Sang Hwi; IM, Junhwan; LEE, Soon Ok; KIM, Jongmin; KO, Kwang Seok; KIM, Byungho; KONG, Minjung; KIM, Mi Sun; MOON, Hyung Jo; (106 pag.)WO2016/89060; (2016); A2;,
Bromide – Wikipedia,
bromide – Wiktionary