1-Bromo-4-fluoro-2-nitrobenzene

light yellow powder

Silak reaction tube equipped with a magnetic stirrer was charged with 6.2 mg of silver sulfate, 36.3 mg of copper acetate, 12.5 mg of 2, 9-dimethyl-1, 10-o-phenanthroline, 37 mg of 2-nitro-4-fluorobenzoic acid and 30.9 mg of sodium bromide4 mL of dimethyl sulfoxide. Heat 160 ° C in the presence of oxygenReaction for 24 hours. After the reaction was completed, distilled water was added to quench the reaction, Extraction with ethyl acetate 3 times, each time 10mL, The combined organic phases were concentrated to give 21.1 mg of 2-nitro-4-fluorobromobenzene, The yield is 48percent.2-Bromo-5-fluorobenzenamine; To a solution of In a of 2-bromo-5-three-neck reaction flask, 2-Bromo-5-fluorobenzenamine. To a solution of General procedure: The catalytic reduction of nitro aromatics was conducted in a 25 mlTelfon-lined stainless steel autoclave with magnetic stirring. In a typicalprocess, 6 mmol nitroarene, and desired amounts of reducing agent andsolvents were introduced in the reactor. The autoclave was transferredinto a water bath at the set temperature with an accuracy of better than0.2 C for '0.5 h. Then, 10 mg catalyst was added into the reactionmixture and started the reduction at a stirring rate of 450 rpm. After thereaction, the catalyst was rapidly separated by ltration. n-Decane(500 muL) as standard was added into the ltrate and was dried withanhydrous Na 2 SO 4 . The products were analyzed by gas chromato-graphy-mass spectrometry (GC-MS) (Shimadzu GCMS-QP2010 Plus)and GC (Varian CP-3800) with a capillary column (column VF-1 ms, 15 m, 0.25 mm, 0.25 mum) and a ame ionization detector (FID).Example S66; Preparation of 4-fluoro-1H-indole-7-carboxylic acid; 1.12 g (5 mmol) of 2-bromo-5-fluoro-nitrobenzene were dissolved in 50 ml THF. At a temperature of -45 C. 15 ml of a 1M vinyl magnesium bromide solution in THF were added under nitrogen in such a way that the temperature did not exceed -40 C. After complete addition the dark solution was stirred for 30 min at -40 C. The reaction mixture was quenched with 10 ml aqueous saturated ammonium chloride solution and extracted twice with diethyl ether. The combined organic layers were washed once with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and the solvent was evaporated. The residue was dissolved in DCM and purified by column chromatography (100 g silica gel; heptane/EtOAc 9:1) to yield 501 mg (47%) 7-bromo-4-fluoro-1H-indole as an orange oil. MS (EI) 213.0 (100), 215.0 (100) (M)+.A solution of Description for D40; 7-Bromo-4-fluoro-1H-indole (D40); Vinylmagnesium bromide (1 M in THF, 681.5 ml.) was added to a solution of 1- bromo-4-fluoro-2-nitrobenzene (D39) (52.0 g) in anhydrous THF (500 ml.) dropwise at -78 0C. The mixture was allowed to warm to room temperature and stirred for 2 hours. TLC indicated the reaction was complete. The reaction mixture was poured into saturated aqueous NH4CI solution. The mixture was extracted with EtOAc (3 * 200 mL). The organic solution was dried over anhydrous sodium sulfate. The dried solution was concentrated. The residue was purified by column chromatography on silica gel to afford 7-bromo-4-fluoro-1 H-indole (D40) (20.0 g) as a white solid.Description for D40; 7-Bromo-4-fluoro-1H-indole (D40); Vinylmagnesium bromide (1 M in THF, 681.5 mL) was added to a solution of STEP C:

Molecular Weight:220.00
XLogP3:2.4
Hydrogen Bond Acceptor Count:3
Exact Mass:218.93312
Monoisotopic Mass:218.93312
Topological Polar Surface Area:45.8
Heavy Atom Count:11
Complexity:161
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes