2-BROMO-5-FLUORO-4-METHYLANILINE

Preparation of Intermediate Compound 28G; 28G; Step A - Synthesis of Compound 9B; 28A 28B; A mixture of compound 28A (6.00 g, 47.9 mmol) and anhydrous potassium carbonate (6.70 g, 48.5 mmol) in anhydrous dichloromethane (130 mL) was cooled to -15 Preparation of Intermediate Compound 9G; 9G; Step A - Synthesis of Compound 9B; A mixture of compound 9A (6.00 g, 47.9 mmol) and anhydrous potassium carbonate (6.70 g, 48.5 mmol) in anhydrous dichloromethane (130 mL) was cooled to -15 Example 28; Preparation of Intermediate Compound 28G A mixture of compound SA (6, 00 g, 47.9 mrnol) and anhydrous potassium carbonate (6.70 g, 48.5 mmoi) in anhydrous dichloromethane (130 mL) was cooled to -15 Preparation of Intermediate Compound AA7; Step A - Synthesis of Compound AA2; A mixture of compound AAl (6.00 g, 47.9 mmol) and anhydrous potassium carbonate (6.70 g, 48.5 mmol) in anhydrous dichloromethane (130 mL) was cooled to -15 Example 19; Preparation of Intermediate Compound AA7; Step A - Synthesis of Compound AA2; A mixture of compound AAl (6.00 g, 47.9 mmol) and anhydrous potassium carbonate (6.70 g, 48.5 mmol) in anhydrous dichloromethane (130 mL) was cooled to -15 A mixture of compound AA1 (6.00 g, 47.9 mmol) and anhydrous potassium carbonate (6.70 g, 48.5 mmol) in anhydrous dichloromethane (130 mL) was cooled to -15° C. in a salt-ice bath and then added dropwise to a solution of bromine (7.70 g, 48.2 mmol) in anhydrous dichloromethane (80 mL). After addition was complete, the reaction was allowed to stir at -15° C. for 1 hour. Ice water (100 mL) was added to the reaction mixture and the aqueous layer was extracted with dichloromethane (2.x.100 mL). The combined organic layers were dried over MgSOTo a suspension of 3-fluoro-4-methylaniline (6.0 g, 48mmol) and K2C03 (6.6 g, 48 mmol) in DCM (80 mL) at -15 °C was added Br2 (2.4 mL, 48mmol) in DCM (20 mL) slowly. The reaction mixture was stirred at -15 °C for 1 h. Themixture was then quenched with ice water (30 mL), diluted with water (80 mL), andextracted with DCM (3 x 50 mL), dried and concentrated. The residue was purified via silica gel chromatography (0 - 10 percent EtOAc in petroleum ether) to give the title compound (3.2 g, 33percent) as a white solid. MS (ES+) C7H7BrFN requires: 203, found: 204 [M+Hf’Example 28; Preparation of Intermediate Compound 28G; 28G; Step A - Synthesis of Compound 9B; 28A 28B; A mixture of compound 28A (6.00 g, 47.9 mmol) and anhydrous potassium carbonate (6.70 g, 48.5 mmol) in anhydrous dichloromethane (130 mL) was cooled to -15 Preparation of Intermediate Compound 9G; 9G; Step A - Synthesis of Compound 9B; A mixture of compound 9A (6.00 g, 47.9 mmol) and anhydrous potassium carbonate (6.70 g, 48.5 mmol) in anhydrous dichloromethane (130 mL) was cooled to -15 Example 28; Preparation of Intermediate Compound 28G A mixture of compound SA (6, 00 g, 47.9 mrnol) and anhydrous potassium carbonate (6.70 g, 48.5 mmoi) in anhydrous dichloromethane (130 mL) was cooled to -15 Preparation of Intermediate Compound AA7; Step A - Synthesis of Compound AA2; A mixture of compound AAl (6.00 g, 47.9 mmol) and anhydrous potassium carbonate (6.70 g, 48.5 mmol) in anhydrous dichloromethane (130 mL) was cooled to -15 Example 19; Preparation of Intermediate Compound AA7; Step A - Synthesis of Compound AA2; A mixture of compound AAl (6.00 g, 47.9 mmol) and anhydrous potassium carbonate (6.70 g, 48.5 mmol) in anhydrous dichloromethane (130 mL) was cooled to -15 A mixture of compound AA1 (6.00 g, 47.9 mmol) and anhydrous potassium carbonate (6.70 g, 48.5 mmol) in anhydrous dichloromethane (130 mL) was cooled to -15° C. in a salt-ice bath and then added dropwise to a solution of bromine (7.70 g, 48.2 mmol) in anhydrous dichloromethane (80 mL). After addition was complete, the reaction was allowed to stir at -15° C. for 1 hour. Ice water (100 mL) was added to the reaction mixture and the aqueous layer was extracted with dichloromethane (2.x.100 mL). The combined organic layers were dried over MgSOTo a suspension of 3-fluoro-4-methylaniline (6.0 g, 48mmol) and K2C03 (6.6 g, 48 mmol) in DCM (80 mL) at -15 °C was added Br2 (2.4 mL, 48mmol) in DCM (20 mL) slowly. The reaction mixture was stirred at -15 °C for 1 h. Themixture was then quenched with ice water (30 mL), diluted with water (80 mL), andextracted with DCM (3 x 50 mL), dried and concentrated. The residue was purified via silica gel chromatography (0 - 10 percent EtOAc in petroleum ether) to give the title compound (3.2 g, 33percent) as a white solid. MS (ES+) C7H7BrFN requires: 203, found: 204 [M+Hf’

Molecular Weight:204.04
XLogP3:2.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:202.97459
Monoisotopic Mass:202.97459
Topological Polar Surface Area:26
Heavy Atom Count:10
Complexity:120
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes