4-Bromoimidazole

Colorless to beige crystalline flakes or powder

To a single-necked flask was added 2, 4, 5-tribromoimidazole (49 g, 161 mmol)Sodium sulfite (101.5 g, 806 mmol)And water (500 ml) were added and stirred at 110 ° C for 6 h, Ethyl acetate was added, The organic layers were combined and dried over anhydrous sodium sulfate, Rotate the ethyl acetate to give compound 6 (20.5 g, yield 89percent)(2) The product of the previous step (4-iodo-1H-imidazole and a little diiodo-substituted imidazole, 78 kg)60 kg of isopropyl alcohol and 240 kg of water were added, Adding 67.5 kg of sodium sulfite, Reflux reaction to raw material disappears.Cooled and filtered (the filtrate used as solvent in the next batch, no emissions)Extraction (using ethyl acetate extraction), Concentration under reduced pressure gave the compound 4-iodo-1H-imidazole (38 kg, purity was 99.2percent by high performance liquid phase).(iv) Production of (2, 3-Dihydronaphtho[2, 3-b]furan-6-yl)(1H-imidazol-4-yl)methanol A solution of (iv) Production of (6, 7-dimethoxynaphthalen-2-yl)(1H-imidazol-4-yl) ketone Example 312A 5-Bromo-4-nitro-1H-imidazole (2.0 g, 13.6 mmol) was reacted with concentrated nitric acid (0.947 ML, 14.96 mmol) in concentrated sulfuric acid (20 ML) at 110 C. for 1 hour.The reaction was cooled to 25 C. and poured into 200 ML of ice water.The resulting white precipitate formed was collected by filtration to give the title compound (2.3 g, 87%). MS (ESI-) m/z 191 (M-H)-. 1H NMR (300 MHz, DMSO-d6) d ppm 7.99 (s, 1H). 10 (1 g, 7 mmol) in 10 mL sulfuric acidwas treated with 70% nitric acid (0.5 mL, 7.7 mmol) and heated at110 C for 1 h. The reaction was cooled to room temperature andpoured intro ice water. The target compound 11 deposited as offwhitesolid was collected by filtration and dried (0.9 g, 67% yield);mp: 273-275 C (lit. mp 271-272 C) [52].To a single-necked flask was added 2, 4, 5-tribromoimidazole (49 g, 161 mmol)Sodium sulfite (101.5 g, 806 mmol)And water (500 ml) were added and stirred at 110 C for 6 h, Ethyl acetate was added, The organic layers were combined and dried over anhydrous sodium sulfate, Rotate the ethyl acetate to give compound 6 (20.5 g, yield 89%)To a reaction flask were added 2, 4, 5-tribromo-1H-imidazole 9(3 g, 10 mmol), sodium sulfite (6.3 g, 50 mmol) and 30 mLwater andthen heated at 110 C for 6 h. After cooling to room temperature, theproduct precipitated as a yellowish solid was filtered and theaqueous phase was extracted by ethyl acetate (3 30 mL). Thecombined organic extracts were washed with water (3 30 mL)and dried over anhydrous magnesium sulfate. Ethyl acetate wasremoved by rotary evaporator and yellowish solid 10 was obtained(1.25 g, 85% yield); mp: 131-132.5 C (lit. mp 130-131 C) [43].

Molecular Weight:146.97
XLogP3:1.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:145.94796
Monoisotopic Mass:145.94796
Topological Polar Surface Area:28.7
Heavy Atom Count:6
Complexity:48.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes