5-broMo-3-fluorobenzene-1,2-diol

To a solution of Compound C2 (40 g, 183 mmol) in THF (260 mL) was added dropwise aq. NaOH solution (0.05 N, 720 mL, 37 mmol) at 0 °C, and then 30percent> HTo a 1 N aqueous solution of sodium hydroxide (230 mL, 0.23 mol), 5-bromo-3-fluoro-2-hydroxybenzaldehyde (45.0 g, 0.21 mol) was added at room temperature, and a 6percent hydrogen peroxide solution (225 mL) was added dropwise over five minutes at room temperature. After the reaction mixture was stirred at room temperature for two hours, a saturated aqueous solution of sodium thiosulfate (150 mL) was added thereto at room temperature. The mixture was extracted three times with ethyl acetate (450 mL), the organic layer was washed sequentially with a 1 N aqueous solution of hydrochloric acid (150 mL) and saturated saline, dried over anhydrous magnesium sulfate, and filtered through silica gel. The solvent was distilled off from the resultant filtrate under reduced pressure to give 39.0 g of the title compound (yield: 92percent). To a solution of 3-fluoro-2-hydroxybenzaldehyde (5 g, 35.6 mmol) in MeCN (40mL) was added NBS (6.008 g, 36 mmol) and CH3CO2NH4 (270 mg, 3.56 mmol) at RT and the mixture was stirred at RT for 2 h, poured into H20 (30 mL) and extracted with EA (20 mL x 2). The organic layers were dried over anhydrous Na2SO4, filtered, concentrated in vacuo, and the residue purified by silica gel column chromatography (PE/EA = 8/1 to 4/1) to afford 5-bromo- 3-fluoro-2-hydroxybenzaldehyde (6.6 g, 85 percent) as a yellow solid. ‘H NMR (400 MI-Tz, DMSO10 d6) ö 11.24 (s, 1H), 10.22 (s, 1H), 7.84 (dd, J= 10.4 Hz, 2.4 Hz, 1H), 7.59 (dd, J 2.4 Hz, 1.6Hz, 1H). LC-MS: tR= 1.284 mm.To a solution of

Molecular Weight:207.00
XLogP3:2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Exact Mass:205.93787
Monoisotopic Mass:205.93787
Topological Polar Surface Area:40.5
Heavy Atom Count:10
Complexity:122
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes