2-Fluoro-3-methoxybenzenamine

Preparation of compound 9[00176] To a compound 8 (24 g, 100 mmol) solution in dichloromethane (100 mL) was slowly added TFA (40 mL) at 0°C. The reaction mixture was stirred at room temperature overnight, then extracted with H00155] Preparation of compound 9[00156] To a compound 8 (24 g, 100 mmol) solution in dichloromethane (100 mL) was slowly added TFA (40 mL) at 0°C. The reaction mixture was stirred at room temperature overnight, then extracted with HCompound D2 (2.28 g, 9. 45 MMOL) was treated with 4N HCI/DIOXANE solution (from Aldrich) (10 mL, 40 mmol) for 60 min and HPLC analysis showed that the starting material was fully consumed. The reaction mixture was concentrated IN VACUO, re- dissolved in EtOAc and washed with water, saturated NaHCO3 (aq), and saturated brine. The organic phase was dried (MGS04), filtered and concentrated to give 1. 18 g (88percent) of D3 as a brown oil, which was used as is in the following step. MS: 141. 9 (M + H) +, 139.9 (M - H)-.Description 40; 2-Fluoro-3-methoxyaniline; To a solution of 2-fluoro-3-methoxy benzoic acid [Synlett (1991), (10), 731-2] (15.0 g, 88 mmol) and triethylamine (13.49 ml, 96.8 mmol) in toluene (300 ml) was added diphenylphosphoryl azide (20.9 ml, 96.8 mmol) and the resulting mixture heated at reflux for 1 hour. After this time 2-methyl-2-propanol (12.5 ml, 132 mmol) was added and heating continued for 5 hours. The mixture was cooled and evaporated, and the residue partitioned between water and dichloromethane. The dichloromethane layer was dried over NazSO4, filtered through a 1 inch plug of silica and evaporated. The residue was dissolved in dichloromethane (200 ml) and trifluoroacetic acid (25 ml) added, and the resulting mixture stirred at room temperature overnight. The mixture was evaporated and the residue partitioned between dichloromethane and sat. K2CO3, the dichloromethane layer was dried over Na2SO4, filtered and evaporated. The residue was purified by column chromatography on silica : (eluent with 15percent EtOAc in isohexanes) to give the title compound as a pale yellow oil (10.8 g, 87percent). 1H NMR (400 MHz, CDCl3) 3.72 (2 H, br s), 3.85 (3 H, s), 6.34-6. 41 (2 H, m), 6.81-6. 86 (1 H, m).

Molecular Weight:141.14
XLogP3:1.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:141.058992041
Monoisotopic Mass:141.058992041
Topological Polar Surface Area:35.2
Heavy Atom Count:10
Complexity:110
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes