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ChemicalBook CAS DataBase List 6-benzyloxy-2-fluorobenzonitrile
94088-45-6

6-benzyloxy-2-fluorobenzonitrile synthesis

2synthesis methods
-

Yield:94088-45-6 96%

Reaction Conditions:

with potassium carbonate;potassium iodide in acetonitrile at 20; for 12 h;

Steps:

1.1 1. Synthesis of 2-(Benzyloxy)-6-fluorobenzonitrile (Compound 4)

To a mixture of 10.00 g (73.0 mmol, 2.0 eq) K2CO3, 200 mg KI and 5.00 g 2-fluoro-6-hydroxybenzonitrile (36.5 mmol, 1.0 eq) in 100 ml acetonitrile, then 6.55 g (38.3 mmol, 1.05 eq) benzyl bromide was added to the mixture, and the whole was stirred at room temperature for 12 h.
After the reaction was complete, most of the solution was removed under reduced pressure, water was added to the residue and extracted with EA, the organic layers washed with saturated sodium chloride solution, dried over Na2SO4, filtered, and concentrated.
The residue was purified with column chromatography (PE/EA = 15:1) to give compound 4, 8.0 g white solid, yield 96%.
The structure is confirmed correct and data are as follow: MS (ESI) (m/z): 228.0 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ 7.73 - 7.62 (m, 1H), 7.43 (d, J = 7.0 Hz, 2H), 7.38 (t, J = 7.4 Hz, 2H), 7.32 (d, J = 7.1 Hz, 1H), 7.16 (d, J = 8.7 Hz, 1H), 7.03 (t, J = 8.8 Hz, 1H), 5.27 (s, 2H).

References:

EP3750890,2020,A1 Location in patent:Paragraph 0030-0032

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