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ChemicalBook CAS DataBase List 3-Bromofluorobenzene
1073-06-9

3-Bromofluorobenzene synthesis

6synthesis methods
-

Yield:1072-85-1 0.06 mmol ,1073-06-9 0.03 mmol ,460-00-4 0.16 mmol ,399-94-0 0.01 mmol ,348-61-8 0.004 mmol

Reaction Conditions:

with xenon difluoride;boron trifluoride diethyl etherate at 0 - 25;Cooling with ice;

Steps:

Reaction of substituted benzenes with xenondifluoride in the presence of boron trifluoride-diethyl ether complex in PFB (procedure A).
General procedure: A FEP or PFA reactor equipped with a Teflon-lined magnetic stir bar and connected to a gas-washing bottle was charged with substituted benzene (0.95-1.10 mmol), 1,1,1,3,3-pentafluorobutane (1-2 mL per mmol of C6H5R), and BF3 · Et2O (1.3-1.5 mmol per mmol of C6H5R). The mixture was stirred for 10-15 min at 0-5°C (ice bath), and XeF2 (1.2-1.3 mmol per mmol of C6H5R) was added in portions. After addition of each portion, the mixture was stirred for 3-5 min at 22-25°C and cooled again. When the addition was complete the dark solution was stirred for 15-30 min at 22-25°C, 10% aqueous KHCO3 was added, and the upper organic layer was separated, passed through a short column charged with silica gel (40-60 μm), and dried over MgSO4. The solution was analyzed by 19F NMR and GC/MS. The main products are given in table, and the others are listed below (GC/MS data).

References:

Bardin;Adonin, N. Yu. [Russian Journal of Organic Chemistry,2016,vol. 52,# 10,p. 1400 - 1407][Zh. Org. Khim.,2016,vol. 52,# 10,p. 1412 - 1419,8]

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