1,4-DIBROMO-2,3-DIFLUOROBENZENE

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 NaHSOIn a 150mL two-neck round-bottom flask, (2, 3-difluoro-1, 4-phenylene)bis(trimethylsilane) 1 (10.34g, 40mmol) was added slowly into bromine (6.3mL, 120mmol) at 0°C. The mixture was heated to 58°C and stirred for 2h. Then bromine (1mL, 20mmol) was added again and stirred for 1h at 58°C. The mixture was cooled down to 0°C and added saturated NaHCOTo neat bromine (76.9 mL, 1.50 mol) cooled to 0° C. in an ice bath was added portion wise solid D-1b (126.23 g, 0.500 mol) while maintaining the internal temperature between 20-45° C. (caution: exothermic). The reaction mixture was stirred at 58° C. for 2 h. After 1 h of this period had elapsed additional bromine (45.48 g) was added and the addition funnel was rinsed with cyclohexane (10 mL). The reaction mixture was cooled to 0° C. and slowly poured into ice-cold saturated NaHSOstep 2-To neat bromine (76.9 mL, 1.50 mol) cooled to 0° C. in an ice bath was added portion wise solid 23b (126.23 g, 0.500 mol) while maintaining the internal temperature between 20-45° C. (caution: exothermic.). The reaction mixture was stirred at 58° C. for 2 h. After 1 h of this period had elapsed additional bromine (45.48 g) was added and the addition funnel was rinse with cyclohexane (10 mL). The reaction mixture was cooled to 0° C. and slowly poured into ice-cold saturated NaHSOstep 2-; To neat bromine (76.9 mL, 1.50 mol) cooled to 0° C. in an ice bath was added portion wise solid 1b (126.23 g, 0.500 mol) while maintaining the internal temperature between 20-45° C. (caution: exothermic). The reaction mixture was stirred at 58° C. for 2 h. After 1 h of this period had elapsed additional bromine (45.48 g) was added and the addition funnel was rinsed with cyclohexane (10 mL). The reaction mixture was cooled to 0° C. and slowly poured into ice-cold saturated NaHSO1, 4-Dibromo-2, 3-difluorobenzene (5) Bromine (9.9 mL) was placed in a 100 mL two-necked round-bottomed flask connected to acondenser and a gatt tube under ice cold condition. 2, 3-Difluoro-1, 4-bis(trimethylsilyl)benzene (4, 5 g, 19.34 mol) was added and the mixture stirred for 1 h58 °C. A further portion of bromine (0.5 mL) was added to the mixture and stirring continuedat the same temperature for 12 h. After cooling to 0 °C the reaction was quenched by theaddition of sodium bicarbonate solution. The mixture was extracted with ethyl acetate, theorganic phase washed with brine and dried over magnesium sulfate. The solution was thenconcentrated under vacuum using a rotary evaporator and the crude product purified bycolumn chromatography. Yield (70percent)

1,4-Dibromo-2,3-difluorobenzene is a halogenated benzene used in the preparation of various biologically active compounds such as non-nucleoside reverse transcriptase inhibitors. 1,4-Dibromo-2,3-difluorobenzene is also used in the synthesis of conjugated polymers for organic photovoltaics.

Molecular Weight:271.88
XLogP3:3.5
Hydrogen Bond Acceptor Count:2
Exact Mass:271.84708
Monoisotopic Mass:269.84913
Heavy Atom Count:10
Complexity:106
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes