6-Bromo-5-fluoroindole

The enamine (1.89 g, 4.38 mmol) was dissolved in EtOH (35.0 ml_). To this solution Fe (4.42 g, 79.0 mmol) and acetic acid (35.0 ml_) were added and the mixture was stirred at 90 Synthesis of 6-Bromo-5-fluoroindole was carried out in this step according to the procedure reported by A. D. 6-Bromo-5-fluoroindole To a andrt solution of 2, 4-dichloro-5-trifluoromethylpyrimidine (945 uL, 7.01 mmol) in anh. (anhydrous) DCE (3 mL) under nitrogen, was added aluminum trichloride (472 mg, 3.51 mmol), and the resulting mixture was stirred at 80 C for 30 min. After this time, the reaction mixture was cooled to RT, and General procedure: 458 mg (2.0 mmol) of methyl 3-(bromomethyl) benzoate (6a) and 382 mg (2.0 mmol) 6-bromoindole (5a) were added into a 50 mL flask, then 5.0 mL anhydrous DMF and 1.38 g (10.0mmol) potassium carbonate were added. The mixture was stirred at room temperature overnight.TLC indicated no starting material remained and the reaction was quenched by adding 25 mLwater. The solution was extracted with ethyl acetate (30 mL ×3) or dichloromethane (30 mL ×3).The organic solvent was combined and evaporated, the product was purified by flash column chromatography using hexane : ethyl acetate (7:1) as eluent. 655.2 mg target compound obtainedas pale yellow oil, yield 95%.

Molecular Weight:214.03
XLogP3:2.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:212.95894
Monoisotopic Mass:212.95894
Topological Polar Surface Area:15.8
Heavy Atom Count:11
Complexity:153
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes