
1,4-DIBROMO-2,3-DIFLUOROBENZENE synthesis
- Product Name:1,4-DIBROMO-2,3-DIFLUOROBENZENE
- CAS Number:156682-52-9
- Molecular formula:C6H2Br2F2
- Molecular Weight:271.88

867366-94-7

156682-52-9
1,4-Dibromo-2,3-difluorobenzene (5) was synthesized as follows: bromine (9.9 mL) was added to a 100 mL two-necked round-bottomed flask, which was connected to a condenser tube and a drying tube under ice bath conditions. Subsequently, 2,3-difluoro-1,4-bis(trimethylmethylsilyl)benzene (4.5 g, 19.34 mmol) was added, and the mixture was stirred at 58 °C for 1 hour. Next, another portion of bromine (0.5 mL) was added to the mixture and stirring was continued at the same temperature for 12 hours. Upon completion of the reaction, the mixture was cooled to 0 °C and the reaction was quenched by addition of sodium bicarbonate solution. The mixture was extracted with ethyl acetate and the organic phase was washed with brine and dried with magnesium sulfate. Subsequently, the solution was concentrated under vacuum using a rotary evaporator and the crude product was purified by column chromatography. The yield of the final product was 70%.

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156682-52-9
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Yield:156682-52-9 90%
Reaction Conditions:
with bromine in tetrahydrofuran at 0 - 60; for 12 h;Solvent;
Steps:
2.4.7. Synthesis of 2,3-difluoro-1,4-dibromobenzene (10)
To a solution of compound 9 (26 g, 98.7 mmol) in 10 mL THF, bromine (14.8 mL, 296.0 mmol) in 10 mL THF was added dropwise at 0 °C. The reaction mixture was stirred for 12 h at 60 °C and slowly poured into saturated NaHSO3 solution at 0 °C. After extraction with 200 mL of CHCl3, the organic phase was washed with 3 x 50 mL of water and dried over MgSO4. After removing the organic solvent under reduced pressure, the residue was purified by flash chromatography to give 24.1 g (90%) of compound 10. 1H NMR (300 MHz, CDCl3): δ (ppm) 7.22 (s, 2H); 13C NMR (75 MHz, CDCl3): δ (ppm) 148.7 (dd, 1JC-F = 254.9 and 2JC-F = 17.3 Hz), 128.3. 109.5 (dd, 2JC-F = 10.4 Hz and 3JC-F = 8.1 Hz). HRMS (m/z, EI+) calcd for C6H2Br2F2 269.8490, found 269.8491.
References:
Jeong, Ina;Chae, Sangmin;Yi, Ahra;Kim, Juae;Chun, Ho Hwan;Cho, Jung Hyeong;Kim, Hyo Jung;Suh, Hongsuk [Polymer,2017,vol. 109,p. 115 - 125]

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156682-52-9
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