4-bromo-2,6-dimethylbenzoic acid

off-white powder

Preparation of 4-bromo-2, 6-dimethylbenzoic acid (B2)(B2)The title compound may be prepared according to Scheme B, as follows. A solution of 5- bromo-2-iodo-l, 3-dimethyl-benzene (Bl) (1.0 mol eq) in methyl-tert-butyl ether (6.0 rel vols) may be added to iso-propylmagnesium chloride (2.0 mol eq) in methyl-tert-butyl ether (2.0 rel vols), maintaining < 0 °C. Carbon dioxide gas may be added until reaction is shown to be complete. 2N aqueous hydrochloric acid may be added (4 rel vols) to quench the reaction, the phases can be separated and the aqueous phase discarded. The product may be extracted into 1M aqueous sodium hydroxide solution (6.5 rel vols), then washed with methyl tert-butyl ether (4 rel vols). The title compound (B2) may be precipitated by the addition of 2N aq hydrochloric acid (4.5 rel vols) before being filtered, washed with water then heptane and dried to yield a white crystalline solid (85percent).1H NMR (400 MHz, CDC1Preparation of 4-bromo-2, 6-dimethylbenzoic acid (B2)(B2)The title compound may be prepared according to Scheme B, as follows. A solution of 5- bromo-2-iodo-l, 3-dimethyl-benzene (Bl) (1.0 mol eq) in methyl-tert-butyl ether (6.0 rel vols) may be added to iso-propylmagnesium chloride (2.0 mol eq) in methyl-tert-butyl ether (2.0 rel vols), maintaining < 0 °C. Carbon dioxide gas may be added until reaction is shown to be complete. 2N aqueous hydrochloric acid may be added (4 rel vols) to quench the reaction, the phases can be separated and the aqueous phase discarded. The product may be extracted into 1M aqueous sodium hydroxide solution (6.5 rel vols), then washed with methyl tert-butyl ether (4 rel vols). The title compound (B2) may be precipitated by the addition of 2N aq hydrochloric acid (4.5 rel vols) before being filtered, washed with water then heptane and dried to yield a white crystalline solid (85percent).1H NMR (400 MHz, CDC10.6 mmol of potassium acetate, 0.3 mmol of 4-bromo-2-methylbenzoic acid, palladium acetate 0.03 mmol, di-tert-butylperoxyEther 0.6 mmol, hexafluoroisopropanol 0.8 mL was added to a 15 mL reaction tube, placed in an oil bath at 80 C, at a pressure of 1 largeThe reaction was carried out in an air atmosphere at atmospheric pressure for 24 hours; after cooling to room temperature, the reaction solution was diluted with ethyl acetate, washed with water and dried with organicNa2SO4 is dried, filtered, concentrated, Purification by thin layer chromatography gave 30.8 mg of the desired product.White solid, The yield was 45%.General procedure: To a 50 mL sealed tube was added 1 (0.15 mmol), acid(0.45 mmol), CuOAc (7.4 mg, 0.06 mmol), AgNO3 (101.9mg, 0.6 mmol), Li2CO3 (33.3 mg, 0.45 mmol) and DMF (3mL). The mixture was purged with N2 and stirred at 120 Cfor 24 h. The reaction mixture was then cooled to roomtemperature, diluted with dichloromethane and quenchedwith saturated sodium sulfide. The aqueous phase was extractedwith dichloromethane (3×10 mL). The combinedorganic phase was dried with anhydrous magnesium sulfate.After concentration, the resulting residue was purified byflash chromatography to afford the product.

Molecular Weight:229.07
XLogP3:2.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:227.97859
Monoisotopic Mass:227.97859
Topological Polar Surface Area:37.3
Heavy Atom Count:12
Complexity:169
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes