1-Bromo-4-(3,3-difluorocyclobutyl)benzene synthesis
- Product Name:1-Bromo-4-(3,3-difluorocyclobutyl)benzene
- CAS Number:1236357-60-0
- Molecular formula:C10H9BrF2
- Molecular Weight:247.08
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Yield:1236357-60-0 82.8%
Reaction Conditions:
with diethylamino-sulfur trifluoride in dichloromethane at -70 - 20; for 24 h;
Steps:
V.19.3 Synthesis of 1-bromo-4-(3, 3-difluorocyclobutyl) benzene [5.19c]
5.19b (0.66 g, 2.93 mmol, 1.0 equiv) was dissolved in dichloromethane (15 mL) and cooled to -70 °C. DAST (1.18 g, 7.33 mmol, 2.5 equiv) was added drop wise and the reaction mixture was stirred at room temperature for 24 hours. The reaction mixture was quenched with water, neutralized by saturated aqueous sodium bicarbonate solution and extracted with dichioromethane. The organic layer was washed with brine, dried over sodium sulfate and concentrated to afford a crude residue. The crude residue was purified by silica gel column chromatography (0-2 % EtOAc/Hexane) to afford the desired product 5.19c (0.6 g, 82.8 % yield). 1H NMR (400 MHz, DMSO) 6 7.53 (d, J = 8.4 Hz, 2H), 7.29 (d, J = 8.3 Hz, 2H), 3.47-3.36 (m, 1H), 3.08-2.91 (m, 2H), 2.67 (dddd, J= 18.4, 14.4, 10.5, 6.2 Hz, 2H).
References:
WO2015/66413,2015,A1 Location in patent:Page/Page column 175; 176
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