4-bromo-2-ethylbenzenemethanol synthesis
- Product Name:4-bromo-2-ethylbenzenemethanol
- CAS Number:877131-21-0
- Molecular formula:C9H11BrO
- Molecular Weight:215.09
194487-79-1
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Yield:877131-21-0 96%
Reaction Conditions:
with diisobutylaluminium hydride in tetrahydrofuran;toluene at -78 - 0;Inert atmosphere;
Steps:
C.C.1.48.C.1.48.5 C.1.48.5. (4-Bromo-2-ethylphenyl)methanol
To a cooled (-78°C) solution of methyl 4-bromo-2-ethylbenzoate (2.219 g, 9.01 mmol) in anh. THF (60 mL) is added dropwise a solution of diisobutylaluminum hydride (1 M in toluene, 27.0 mL, 27.0 mmol). The mixture is further stirred at -78°C, under nitrogen, for 15 min and is then allowed to warm-up to 0°C. Stirring at 0°C is continued for 45 min, and the cooled RM is treated successively with water (1 mL), 2.8 N aq. NaOH (1 mL) and water (3 mL). The mixture is then allowed to warm-up to RT and is further stirred for 30 min. The resulting mixture is filtered over celite, washing with THF and the filtrate is concentrated to dryness under reduced pressure. EtOAc and water are added and the layers are separated. The aqueous layer is extracted twice with EtOAc and the combined organic layers are dried over anh. MgSC>4, filtered and concentrated under reduced pressure. Purification by FC (from heptane to heptane/EtOAc = 1/1) affords (4-bromo-2- ethylphenyl)methanol (1.854 g, 96%). LC-MS B: tR = 0.84 min; no ionization.
References:
WO2018/210987,2018,A1 Location in patent:Page/Page column 123
644984-78-1
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68837-59-2
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