Methyl 3-(2-cyanopropan-2-yl)benzoate synthesis
- Product Name:Methyl 3-(2-cyanopropan-2-yl)benzoate
- CAS Number:872091-85-5
- Molecular formula:C12H13NO2
- Molecular Weight:203.24
Yield:872091-85-5 93.1 %
Reaction Conditions:
with sulfuric acid at 60;Reagent/catalyst;Temperature;
Steps:
55.2 Step 2: Preparation of methyl 3-(2-cyanopropan-2-yl)benzoate (Intermediate C)
To a solution of Intermediate B (5 g, 26.43 mmol) in MeOH (50 mL) was added H2SO4 (920.00 mg, 9.38 mmol, 0.5 mL) . The mixture was stirred at 60 °C for 8 hr. The reaction mixture was concentrated to remove MeOH and diluted with aq. NaHCO3 (20 mL) and extracted with EA (20 mL_x2). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to give the residue. The residue was purified by flash silica gel chromatography (ISCO; 80 g SepaFlash Silica Flash Column, Eluent of 0~50% Ethylacetate/Petroleum ether gradient 60 mL/min) and concentrated to afford Intermediate C (5 g, 24.60 mmol, 93.10% yield) as colorless oil. LCMS (ESI) m/z [M+H]+=204.1 . 1H NMR (400MHz, CDCI3) δ = 8.12-8.01 (m, 1 H), 8.01-7.99 (m, 1 H), 7.52-7.50 (m, 1 H), (0450) 7.48-7.46 (m, 1 H), 3.94 (s, 3H), 1.76 (s, 6H) ppm.
References:
WO2021/155316,2021,A1 Location in patent:Paragraph 147-148
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