3,5-DibroMo-4-Methoxybenzaldehyde

2, 4-dibromo-3-methoxy-benzaldehyde (Compound 1) was dissolved in dry DMF, Add excess methyl iodide and potassium carbonate, stir under nitrogen at room temperature overnight, Extraction gave compound 2.(2) To a solution of 3, 5-dibromo-4-hydroxybenzaldehyde (1.00 g, 3.57 mmol) and methyl iodide (MeI, 0.5 mL, 1.14 g, 8.03 mmol) in DMF (15 mL) was added anhydrous potassium carbonate (K3, 5-Dibromo-4-hydroxybenzaldehyde(1.40 g, 5.01 mmol), iodomethane (0.37 mL, 5.94 mmol), and KPotassium carbonate (100mg, 0.72mmol) was added to a solution of 3, 5-dibromo-4-hydroxybenzaldehyde (100mg, 0.36mmol) and methyl iodide (51µL, 0.81mmol) in DMF (1.5mL). The mixture was stirred at 55 °C for 3h. After cooling to room temperature water (8mL) was added and the resulting precipitate was filtered and dried in vacuum to give 85mg (81percent) as a colorless solid. HPLC: RBromine (1.63 mL, 31.5 mmol) in acetic acid (5 mL) was added dropwise to a mixture of 4-hydroxybenzaldehyde (1.85 g, 15 mmol) and sodium acetate (3.85 g, 46.5 mmol) in acid acetic (35 mL) at room temperature over 20 min. The reaction mixture was stirred for 1 h at room temperature. HTo a solution of 3, 5-dibromo-4-hydroxybenzaldehyde (1.00 g, 3.57 mmol) and methyl iodide (MeI, 0.5 mL, 1.14 g, 8.03 mmol) in DMF (15 mL) was added anhydrous potassium carbonate (K2CO3, 0.992 g, 7.18 mmol). The reaction mixture was stirred at 55 C for 3 h, cooled to room temperature, and quenched by addition of water (80 mL). The resultant white precipitate was filtered under vacuum, washed with water (40 mL), and dried to give the anisaldehyde intermediate (1.02 g, 3.47 mmol, 97%) as a white solid: mp 90-91 C; IR (NaCl) 1688 cm-1 (CO), 1546 cm-1 (CC); 1H NMR (300 MHz, CDCl3) delta 9.86 (s, 1H, CHO), 8.03 (s, 2H, ArH), 3.97 (s, 3H, OCH3); 13C NMR (75 MHz, CDCl3) delta 188.6 (CHO), 159.2 (C), 134.3 (C), 134.0 (CH), 119.3 (C), 60.8 (OCH3). To a solution of this material (0.100 g, 0.340 mmol) in EtOH (3.5 mL) at 0 C was added sodium borohydride (NaBH4, 0.022 g, 0.592 mmol). The reaction mixture was stirred at room temperature for 5 h, quenched by addition of 3% aqueous HCl (5 mL), extracted with ethyl acetate (50 mL), washed with water (50 mL), saturated aqueous NaHCO3 (30 mL), and brine (30 mL), dried over Na2SO4, filtered, and concentrated in vacuo to give the alcohol intermediate (0.098 g, 0.331 mmol, 97%) as a white solid: mp 38-39 C; IR (NaCl) 3350 cm-1 (O-H), 1548 cm-1 (CC); 1H NMR (300 MHz, CDCl3) delta 7.51 (s, 2H, ArH), 4.62 (s, 2H, ArCH2), 3.88 (s, 3H, OCH3), 1.90 (br s, 1H, OH); 13C NMR (75 MHz, CDCl3) delta 139.6 (C), 130.9 (CH), 118.1 (C), 63.3 (CH2), 60.6 (OCH3).

Molecular Weight:293.94
XLogP3:2.7
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:293.87141
Monoisotopic Mass:291.87345
Topological Polar Surface Area:26.3
Heavy Atom Count:12
Complexity:151
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes