(3-broMo-5-Methoxyphenyl)Methanol synthesis

5synthesis methods

Product Name:(3-broMo-5-Methoxyphenyl)Methanol
CAS Number:262450-64-6
Molecular formula:C8H9BrO2
Molecular Weight:217.06

157893-14-6
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$10.00/250mg

262450-64-6
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$62.50/1g

Yield:262450-64-6 92%

Reaction Conditions:

with dimethylsulfide borane complex in tetrahydrofuran at 20 - 65; for 5 h;Inert atmosphere;

Steps:

66.66A (3-Bromo-5-methoxyphenyl)methanol

Boron methyl sulfide complex (1.4 ml, 14.00 mmol) was added dropwise to a solution of 3 -bromo-5 -methoxybenzoic acid (0.866 g, 3.75 mmol) in THF (20 ml, 244 mmol) under nitrogen at room temperature. The resulting mixture was stirred at 65 °C for 5h. At 0 °C, water was added dropwise and the reaction mixture was concentrated in vacuo. The residue was diluted in AcOEt and washed successively with 1N NaOH, 1N HCl, sat. NaHCO3 and brine, dried over anh. Na₂SO₄ and concentrated. The residue was purified on ISCO using a REDISEP Gold 24 g column (Hex/EtOAc). The title material (0.746g, 92%) was obtained as a white solid after concentration of the fractions. LC (Method B): 1.749 min. ¹H NMR (400 MHz, acetone) δ ppm 7.11 (dq, J=2.1 , 0.9 Hz,1H) 6.97 (t, J=2.2 Hz,1H) 6.93 (dq, J=2.3, 1.1 Hz,1H) 4.57 - 4.63 (m, 2H) 4.33 (t, J=5.9 Hz, 1H) 3.81 (s, 3H).

References:

WO2013/163241,2013,A1 Location in patent:Paragraph 00152

56709-70-7 Synthesis