ChemicalBook CAS DataBase List benzyl 3,3-difluorocyclobutanecarboxylate

benzyl 3,3-difluorocyclobutanecarboxylate synthesis

5synthesis methods

Product Name:benzyl 3,3-difluorocyclobutanecarboxylate
CAS Number:935273-86-2
Molecular formula:C12H12F2O2
Molecular Weight:226.22

198995-91-4
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$18.00/250mg

benzyl 3,3-difluorocyclobutanecarboxylate

935273-86-2
62 suppliers
$44.00/250mg

Yield:935273-86-2 71%

Reaction Conditions:

with diethylamino-sulfur trifluoride in dichloromethane at 20; for 16 h;Inert atmosphere;

Steps:

B.B Step B: Benzyl 3,3-difluorocyclobutanecarboxylate.

To a solution of benzyl 3- oxocyclobutanecarboxylate (1.23g, 6.03 mmol) in DCM (35 mL) was added DAST (0.8 mL, 6.03 mmol) dropwise under nitrogen. The mixture was stirred at r.t. for 16 h and then diluted with DCM. After washed successively in sequence with saturated sodium bicarbonate, IN aq. hydrochloric acid, and brine, the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by silica gel chromatography with 93% hexane / EtOAc as eluent to give the desired compound as an oil (1 g, 71% yield). 1H NMR (400 MHz, CDC1₃): δ 7.47 - 7.27 (m, 5H), 5.16 (s, 2H), 3.09 - 2.95 (m, 1H), 2.90 - 2.60 (m, 4H).

References:

WO2013/107405,2013,A1 Location in patent:Page/Page column 42