5,7-Dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxine

Needle-like solid

A THF (20 mL) solution of 3, 4-ethoxylene dioxy thiophene(1.42 g, 10.60 mmol), N-bromosuccinimide (3.74 g, 12.80 mmol) andacetic acid (20 mL) were charged sequentially into a round-bottomflask. The mixturewas stirred for 2 h at room temperature. After thereaction, pouring the reaction mixture into distilled water andstirring with a glass rod, precipitate was filtered to afford A4 as awhite solid (2.50 g, 8.30 mmol, yield 83percent). 1H NMR (400 MHz, CDCl3, ppm): δ = 4.27 (s, 4H).General procedure: In a 150 mL 3-neckedflask, a solution of thienothiophene(TT) (11.2 g, 80 mmol) in dry THF (100 mL) was cooled to 10 °C under a nitrogenatmosphere. NBS (35.6 g, 200 mmol) was addedslowly in portions and allowed to stir for 8 h at approximately 10 °C. Thereaction mixture was then poured into dichloromethane (DCM).The organic layer was washed with water and dried over anhydrous MgSOA mixture of bromosuccinimide (NBS) (2.75 g, 15.45 mmol) and N, N-dimethylformamide (DMF) (15 ml) was added dropwise to the mixture of EDOT (1.0 g, 7.03 mmol) and DMF (15 ml) and the reaction temperature was kept between 18-23 °C.

5,7-Dibromo-2,3-dihydrothieno[3,4-b]-1,4-dioxine is used in the preparation of 3,4-ethylenedioxythiophene oligomers with optical and redox properties.

Molecular Weight:299.97
XLogP3:3.4
Hydrogen Bond Acceptor Count:3
Exact Mass:299.82783
Monoisotopic Mass:297.82988
Topological Polar Surface Area:46.7
Heavy Atom Count:11
Complexity:142
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes