Ethyl 3-broMo-4-cyanobenzoate

Preparation of 3-Bromo-4-cyanobenzoic acid; A solution of ethyl 4-amino-3-bromobenzoate (23.5 g, 96.3 mmol) in methylene chloride at -10° C. is treated dropwise with tert-butyl nitrite (14.0 mL, 118.4 mmol), followed by boron trifluoride diethyl etherate (18.4 mL, 146.5 mmol). The reaction mixture is allowed to come to room temperature, stirred for 4 h, diluted with ethyl ether and filtered. The filtercake is dried, dispersed in toluene, cooled to 0° C., treated with a solution of copper (I) cyanide (11.5 g, 129.2 mmol) and sodium cyanide (15.8 g, 323.1 mmol) in water, stirred at 0° C. for 30 min., warmed to 60° C., stirred for 1 h, cooled to room temperature and diluted with EtOAc and water. The organic phase is separated, dried over MgSOEXAMPLE 200A 2-bromo-4-formylbenzonitrile A solution of compound 87C (5.1 g, 20.0 mmol) in dichloromethane (150 mL) at -100 C. was treated dropwise with 1M DIBAL-H in toluene (26.0 mL, 26.0 mmol), stirred for 30 minutes, treated with methanol (20 mL), stirred for 10 minutes, treated with saturated potassium sodium tartrate, warmed to room temperature, extracted with ethyl acetate, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 4:1/hexanes:ethyl acetate to provide the desired product. 1H NMR (300 MHz, CDCl3) delta 10.04 (s, 1H), 8.17 (d, 1H), 7.93 (dd, 1H), 7.86 (d, 1H).To a stirred solution of

Molecular Weight:254.08
XLogP3:2.6
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:252.97384
Monoisotopic Mass:252.97384
Topological Polar Surface Area:50.1
Heavy Atom Count:14
Complexity:258
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes