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ChemicalBook CAS DataBase List 4-BroMo-3,5-diMethylbenzyl alcohol
27006-02-6

4-BroMo-3,5-diMethylbenzyl alcohol synthesis

7synthesis methods
-

Yield:27006-02-6 100%

Reaction Conditions:

with sodium tetrahydroborate in tetrahydrofuran;water at 0 - 20; for 0.5 h;

Steps:



To a stirred solution of (4-bromo-3,5-dimethylphenyl)methylene diacetate (30) (315 mg, 1.00 mmol) in THF (15 mL) was added NaBH4 (110 mg, 2.91 mmol) in water (1.5 ml) and MeOH (1.5 ml) at 0°C. The mixture was stirred at room temperature for 0.5 h. To the mixture was added water and EtOAc, and extracted with Et2O. The organic layers were washed with brine, dried over MgSO4, filtered and concentrated to afford (4-bromo-3,5-dimethylphenyl)methanol (31) (217 mg, 100% yield). 1H NMR (300 MHz, CDCl3) δ 7.08 (s, 2H), 4.60 (d, J = 5.7, 2H), 2.42 (s, 6H), 1.60 (t, J = 5.7, 1H).

References:

Kawate, Tomohiko;Iwase, Noriaki;Shimizu, Motohisa;Stanley, Sarah A.;Wellington, Samantha;Kazyanskaya, Edward;Hung, Deborah T. [Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,# 22,p. 6052 - 6059] Location in patent:supporting information