4-BENZYLOXY-3-METHOXY-BENZONITRILE synthesis
- Product Name:4-BENZYLOXY-3-METHOXY-BENZONITRILE
- CAS Number:52805-34-2
- Molecular formula:C15H13NO2
- Molecular Weight:239.27
Yield:52805-34-2 100%
Reaction Conditions:
with potassium carbonate in N,N-dimethyl-formamide at 20;
Steps:
C. Synthetic Procedures 4-Benzyloxy-3-methoxybenzonitrile5 (5)
4-Hydroxy-3-methoxybenzonitrile (3.4 g, 22.8 mmol) was dissolved in DMF (45 mL), potassium carbonate (4.73 g, 34.2 mmol) was added slowly, followed by benzyl bromide (3.0 mL, 25.1 mmol). The reaction mixture was stirred overnight at ambient temperature then brine (50 mL) solution was added. The precipitate was collected affording the title compound as a white solid (5.45 g, 100%). Mp: 81-83 °C (lit 81-83 °C 6); 1H NMR (500 MHz, CDCl3) δ: 3.91 (s, 3H, OCH3), 5.21 (s, 2H, Ar-CH2), 6.92 (d, 1H, ArH, J = 8.3 Hz), 7.11 (d, 1H, ArH, J = 1.9 Hz), 7.22 (dd, 1H, ArH, J = 1.9, 8.3 Hz), 7.30-7.46 (m, 5H, ArH). 13C NMR (125 MHz, CDCl3) δ: 56.20, 70.89, 104.18, 113.32, 114.40, 119.23, 126.27, 127.25, 128.77, 128.80, 135.81, 149.68, 152.00. HRMS (ESI, m/z): calc’d for C15H14NO2 [M+H]+ 240.1019 found: 240.1017
References:
Brocklesby, Kayleigh L.;Waby, Jennifer S.;Cawthorne, Chris;Smith, Graham [Tetrahedron Letters,2017,vol. 58,# 15,p. 1467 - 1469] Location in patent:supporting information
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