Benzene, 1-fluoro-5-methoxy-2-methyl-4-nitro- (9CI)

5-Fluoro-4-methyl-2-nitrophenol (2.83 g, 16.5 mmol) was dissolved in N, N-dimethylformamide (25 mL). KStep B/lntermediate B1 12: 1-fluoro-2-methyl-5-(methyloxy)-4-nitrobenzene; 5-fluoro-4-methyl-2-nitrophenol (2.83 g, 16.5 mmol) was dissolved in N, N- dimethylformamide (25 ml_). Potassium carbonate (3.4 g, 25 mmol) and 5-Fluoro-4-methyl-2-nιtrophenol (2 83 g, 16 5 mmol) was dissolved in DMF (25 mL) K(0664) 5-Fluoro-4-methyl-2-nitrophenol (4.48 g, 26.2 mmol) was dissolved in N, N-dimethylformamide (50 mL), and potassium carbonate (5.4 g, 39.3 mmol) and iodomethane (4.46 g, 31.4 mmol) were added to the system. The mixture was stirred at room temperature for 16 h. After the reaction, the reaction solution was poured into water (100 mL), and stirred until solids were precipitated. Filtration was performed and the filter cake was washed with water and dried to get the title compound (4.2 g, yield: 87percent).Step 1: Intermediate 7 1-Fluoro-5-methoxy-2-methyl-4-nitrobenzene Hydrogen fluoride (70percent) in pyridine (47.4 ml, 0.48 mol) in a plastic separatory funnel was added dropwise over 20 min. to pyridine (16 mL) in a plastic bottle at -78° C. (dry ice/acetone bath) under nitrogen. Note: reaction was exothermic. After the addition was complete, the reaction was stirred for 10 min. at -78° C. 5-Methoxy-2-methyl-4-nitroaniline (9.11 g, 0.05 mol) was then added and the reaction mixture was stirred for an additional 10 min. at -78° C. Sodium nitrite (5.8 g, 0.08 mol) was then added and the reaction mixture was stirred an additional 10 min. at -78° C. The reaction mixture was allowed to warm to RT and then heated to 60° C. for 2 h. The reaction mixture was then allowed to cool to RT and an ice/water mixture (300 mL) was added. The resultant precipitates were collected by vacuum filtration, washed with water and dried under vacuum. The solid product was recrystallized from methylcyclohexane to give yellow crystals as the title product (5.8 g, 63percent).

Molecular Weight:185.15
XLogP3:2.2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:185.04882128
Monoisotopic Mass:185.04882128
Topological Polar Surface Area:55
Heavy Atom Count:13
Complexity:194
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes