TERT-BUTYL 4-CYANO-3-FLUOROBENZYLCARBAMATE synthesis

5synthesis methods

Product Name:TERT-BUTYL 4-CYANO-3-FLUOROBENZYLCARBAMATE
CAS Number:229623-55-6
Molecular formula:C13H15FN2O2
Molecular Weight:250.27

24424-99-5 Synthesis

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TERT-BUTYL 4-CYANO-3-FLUOROBENZYLCARBAMATE

229623-55-6
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Yield:229623-55-6 73%

Reaction Conditions:

with N-ethyl-N,N-diisopropylamine in acetonitrile at 20; for 16 h;Inert atmosphere;

Steps:

103.1 Example 103.

Step 1
To a solution of 4-(aminomethyl)-2-fluorobenzonitrile (986.0 mg, 6.57 mmol) in MeCN (5.5 mL) was added DIEA (1.2 mL, 6.89 mmol) and di-tert-butyl dicarbonate (1.44 g, 6.60 mmol) at room temp.
After purging with N2, the reaction was stirred at room temp for 16 h.
Volatiles was evaporated under vacuum.
The crude product was diluted with EtOAc (200 mL) and washed with 10% KHSO₄ solution (100 mL, 2 times).
The organic layer was washed with brine, dried (Na₂SO₄), vacuum filtered, and evaporated under vacuum.
The crude product was dissolved in CH₂Cl₂ and adsorbed on silica gel.
Purification by chromatography (0-15% MeOH-CH₂Cl₂) afforded tert-butyl (4-cyano-3-fluorobenzyl)carbamate (1.19 g, 73% yield).