7-Bromo-2-iodo-9,9-dimethyl-9H-fluorene

Synthesis of Intermediate 1; 30.27 g (110.8 mmol) of 2-bromo-9, 9-dimethyl-9-fluorene, 16.9 g (66.5mmol) of I2, and 15.2 g (66.5mmol) of H5IO6 were dissolved in acetic acid (AcOH). A dilution of H2SO4 in H2O was dropwise added into the solution and stirred at 50°C for 5 hours, and then pure water was added to the reaction solution to obtain solid precipitates. The precipitates were collected and filtered to obtain 37.6 g (yield 85percent) of intermediate 1, and this compound was identified using high-resolution mass spectra (HR-MS).0153] In an argon atmosphere, 23 g (90.6 mmol) of iodine, 9.4 g (41.2 mmol) of periodic acid dihydrate, 42 ml of water, 360 ml of acetic acid, and 11 ml of sulfuric acid were added to 55 g (201.3 mmol) of 2-bromo-9, 9-dimethylfluorene, and the resultant mixture was stirred at 65 °C for 30 min and further stirred at 90 °C for 6 h. [0154] After the reaction, the reaction product was poured into iced water. The precipitated crystals were collected by filtration and washed with water and then with methanol, to obtain 61 g of a white solid, which was identified as the following intermediate 1-1 by FD-MS analysis (yield: 76percent).[0179] In an argon atmosphere, 55 g (201.3 mmol) of 2-bromo-9, 9-dimethylfluorene was added with 23 g (90.6 mmol)of iodine, 9.4 g (41.2 mmol) of periodic acid dihydrate, 42 ml of water, 360 ml of acetic acid, and 11 ml of sulfuric acid.The resultant mixture was stirred at 65 °C for 30 min and further stirred at 90 °C for 6 h.[0180] After the reaction, the reaction product was poured into iced water. The precipitated crystals were collected byfiltration and washed with water and then methanol to obtain 61 g of white solid, which was identified as the following intermediate 1-1 by FD-MS (Field Desorption Mass Spectrometry) (yield: 76percent).Intermediate Synthesis Example 1-1 (Synthesis of Intermediate 1-1)Under an argon atmosphere, 55 g of 2-bromo-9, 9-dimethylfluorene, 23 g of iodine, 9.4 g of periodic acid dihydrate, 42 mL of water, 360 mL of acetic acid and 11 mL of sulfuric acid were placed in a 1, 000 mL three-neck flask, stirred at 65°C for 30 minutes, and then reacted at 90°C for 6 hours. The reaction product was placed in iced water and filtered. The product was rinsed with water and the rinsed with methanol, thereby providing 67 g of white powder. It was identified as Intermediate 1 by FD-MS (field desorption mass spectroscopy) analysis.In an argon atmosphere, 23 g of iodine, 9.4 g of periodic acid dihydrate, 42 mL of water, 360 mL of acetic acid, and 11 mL of sulfuric acid were added to 55 g of 2-bromo-9, 9-dimethylfluorene. The resultant mixture was stirred at 65°C for 30 min and then the reaction was allowed to proceed at 90 °C for 6 h. The reaction product was poured in to icedwater and then filtered. The collected solid was washed with water and then methanol, to obtain 61 g of white powder, which was identified as Intermediate 5 shown below by FD-MS analysis.

Molecular Weight:399.06
XLogP3:5.8
Exact Mass:397.91671
Monoisotopic Mass:397.91671
Heavy Atom Count:17
Complexity:301
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes