4-(Benzyloxy)-3-methoxy-2-nitrobenzaldehyde

Step 3: Preparation of 4-(benzyloxy)-3-methoxy-2-nitrobenzaldehvde; 4-Hydroxy-3-methoxy-2-nitrobenzaldehyde (155 g, 786 mmol) was dissolved in DMF (1500 mL) and the stirred solution was treated with potassium carbonate (217 g, 1.57 mol) followed by benzyl bromide (161 g, 0.94 mol). After stirring for 16 h the reaction mixture was concentrated under reduced pressure and separated between water (2 L) and EtOAc (2 L). The organic layer was washed with brine (3 x 2 L), dried (sodium sulfate) and concentrated under reduced pressure. The resulting solids were triturated with EtStep 3: Preparation of 4-(benzyloxy)-3-methoxy-2-nitrobenzaldehyde4-Hydroxy-3-methoxy-2-nitrobenzaldehyde (155 g, 786 mmol) was dissolved in DM F (1500 mL) and the stirred solution was treated with potassium carbonate (217 g, 1.57 mol) followed by benzyl bromide (161 g, 0.94 mol). After stirring for 16 h the reaction mixture was concentrated under reduced pressure and separated between water (2 L) and EtOAc (2 L). The organic layer was washed with a saturated sodium chloride solution (3 x 2 L), dried (anh. sodium sulfate) and concentrated under reduced pressure. The resulting solids were triturated with EtStep 3: Preparation of 4-(benzyloxy)-3-methoxy-2-nitrobenzaldehyde4-Hydroxy-3-methoxy-2-nitrobenzaldehyde (155 g, 786 mmol) was dissolved in DMF (1500 mL) and the stirred solution was treated with potassium carbonate (217 g, 1.57 mol) followed by benzyl bromide (161 g, 0.94 mol). After stirring for 16 h the reaction mixture was concentrated under reduced pressure and separated between water (2 L) and EtOAc (2 L). The organic layer was washed with a saturated sodium chloride solution (3 x 2 L), dried (anh. sodium sulfate) and concentrated under reduced pressure. The resulting solids were triturated with EtStep 3: Preparation of 4-(benzvloxy)-3-methoxv-2-nitrobenzaldehvde4-Hydroxy-3-methoxy-2-nitrobenzaldehyde (155 g, 786 mmol) was dissolved in DMF (1500 mL) and the stirred solution was treated with potassium carbonate (217 g, 1.57 mol) followed by benzyl bromide (161 g, 0.94 mol). After stirring for 16 h the reaction mixture was concentrated under reduced pressure and separated between water (2 L) and EtOAc (2 L). The organic layer was washed with a saturated sodium chloride solution (3 x 2 L), dried (anh. sodium sulfate) and concentrated under reduced pressure. The resulting solids were triturated with Et10 g of compound (3) were dissolved in 45 mL DMF at 25 . This solution was charged with 14 g potassium carbonate and the temperature did rise to app. 30 . Into this suspension 7.1 mL benzyl bromide was dosed in 15 minutes at a temperature of 30 . The reaction mixture was stirred for 2 hours to complete the reaction. After cooling to 25 125 mL water was added. The suspension was filtered, washed twice with 50 mL water and once with water / methanol (10 mL / 1 0 mL) and dried at 40 under reduced pressure. In this way 14.2 g (97 percent yield) of (4) were obtained as a yellowish solid. 1 H-NMR (500 MHz, d6-DMSO): 3.86 (s, 3H); 5.38 (s, 2 H); 7.45 (m, 5H); 7.62 (d, 2H); 7.91 (d, 2H); 9.81 (s, 1 H).Example 3 : Step A3 : Preparation of 4-(benzyloxy)-3-methoxy-2- nitrobenzaldehyde (4) : 10 g of 3 were dissolved in 45 mL DMF at 25 °C. This solution was charged with 14 g potassium carbonate and the temperature did rise to app. 30 °C. Into this suspension 7.1 mL benzyl bromide was dosed in 15minutes at a temperature of 30 °C. The reaction mixture was stirred for 2 hours to complete the reaction. After cooling to 25 °C 125 mL water was added. The suspension was filtered, washed twice with 50 mL water and once with water / methanol (10 mL / 10 mL) and tried at 40 °C under reduced pressure. In this way 14.2 g (97percent yield) of 4 were obtained as a yellowish solid. 1 H-NMR (500 MHz, d6-DMSO): 3.86 (s, 3H); 5.38 (s, 2 H); 7.45 (m, 5H); 7.62 (d, 2H); 7.91 (d, 2H); 9.81 (s, 1 H).10 g of compound (3) were dissolved in 45 mL DMF at 25 . This solution was charged with 14 g potassium carbonate and the temperature did rise to app. 30 . Into this suspension 7.1 mL benzyl bromide was dosed in 15 minutes at a temperature of 30 . The reaction mixture was stir red for 2 hours to complete the reaction. After cooling to 25 125 mL water w as added. The suspension was filtered, washed twice with 50 mL water and once with water / methanol (10 mL / 10 mL) and dried at 40 under reduced pressu re. In this way 14.2 g (97percent yield) of (4) were obtained as a yellowish solid.1 H-NMR (500 MHz, d6-DMSO): 3.86 (s, 3H); 5.38 (s, 2 H); 7.45 (m, 5H); 7.62 (d, 2H); 7.91 (d, 2H); 9.81 (s, 1 H).

Molecular Weight:287.27
XLogP3:2.6
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:5
Exact Mass:287.07937252
Monoisotopic Mass:287.07937252
Topological Polar Surface Area:81.4
Heavy Atom Count:21
Complexity:351
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes