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

3-Bromofluorobenzene synthesis

6synthesis methods
Iodonium, (3-fluorophenyl)(2,4,6-trimethylphenyl)-, 1,1,1-trifluoromethanesulfonate (1:1)

1430342-19-0

3-Bromofluorobenzene

1073-06-9

The general procedure for the synthesis of m-bromofluorobenzene from the compound (CAS: 1430342-19-0) is as follows: a mixture of diaryliodonium salt (0.5 mmol), methylene halide (0.75 mmol) and acetonitrile (1 mL) was added to a 10 mL reaction tube and heated at 80 °C for 2 h with vigorous stirring. After completion of the reaction (monitored by TLC or GC), the reaction mixture was cooled to room temperature and 5 mL of water was added. After stirring for 10 min, the product was extracted with ethyl acetate (3 x 10 mL). The organic layers were combined, washed with water and dried with anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography using petroleum ether and ethyl acetate as eluents to give purified m-bromofluorobenzene. The structure of the product was confirmed by 1H NMR and 13C NMR.

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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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