3-Bromo-4-(phenylmethoxy)-benzonitrile synthesis
- Product Name:3-Bromo-4-(phenylmethoxy)-benzonitrile
- CAS Number:317358-76-2
- Molecular formula:C14H10BrNO
- Molecular Weight:288.14
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Yield:317358-76-2 95%
Reaction Conditions:
with potassium carbonate in acetone; for 20 h;Inert atmosphere;Reflux;
Steps:
Synthesis of 4-(Benzyloxy)-3-bromobenzonitrile (8)
To a solution of 4-hydroxy-3-bromobenzonitrile (2.43g, 12.3mmol, 1.0 equiv) in acetone (25mL) was added potassium carbonate (5.09g, 36.8mmol, 3.0 equiv) and benzyl bromide (2.31g, 1.6mL, 13.5mmol, 1.07 equiv) and the mixture was stirred at reflux for 20h. After cooling to room temperature, the solvent was filtered and evaporated and redissolved in EtOAc (10mL) followed by washing with water (2×10mL). The combined organic layer was dried (MgSO4) and concentrated in vacuo. The crude product was purified by recrystallization from CH2Cl2 to afford the title compound 8 as a pale yellow solid (3.34g, 95%). The spectroscopic data of this compound matched with those in the literature [18]. Rf=0.27 (EtOAc:PS=15:85). mp: 98-100°C. IR (neat): νmax 3062, 2224, 1595, 1492, 1452, 1381, 1258, 998, 812, 737, 695cm-1. 1H NMR (500MHz, CDCl3): δ 7.84 (d, J=2.1Hz, 1H, H-2), 7.54 (dd, J=8.6, 2.1Hz, 1H, H-6), 7.47-7.32 (m, 5H, ArH), 6.97 (d, J=8.6Hz, 1H, H-5), 5.22 (s, 2H, PhCH2O). 13C NMR (125MHz, CDCl3): δ 158.6 (C-4), 136.9 (C-2), 135.3 (ArC), 133.1 (C-6), 128.9 (2× ArCH), 128.5 ArCH), 127.1 (2× ArCH), 117.8 (C≡N), 113.5 (C-5), 113.0 (C-3), 105.6 (C-1), 71.1 (PhCH2O).
References:
Thaima, Thanaphat;Willis, Anthony C.;Pyne, Stephen G. [Tetrahedron,2019,vol. 75,# 36,art. no. 130476]
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2973-78-6
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100-39-0
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$10.00/10g
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