Application of 148547-19-7, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 148547-19-7, name is Methyl 4-bromo-3-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.
Methyl 4-bromo-3-methylbenzoate (ABCR, 4.90 g; 21.39 mmol; 1 eq.), 2- methoxyphenylboronic acid (3.575 g; 23.53 mmol; 1.10 eq.), potassium carbonate (14.781 mg; 107 mmol; 5 eq.), tetrakis(tripnenylphosphine)palladium(0) (2.5 mg; 2.14 mmol; 0.10 eq.) were mixed in toluene (24.5 mL) and water (24.5 mL) under N2 atmosphere. The reaction mixture was degassed with N2for 10 min and was heated under reflux for 6 hours. The reaction mixture was cooled to RT, filtered over a pad of celite and washed with toluene (500 mL). The filtrate was concentrated under vacuum to afford brown oil. It was taken in EtOAc (500 mL). The organic layer was washed with a saturated aqueous solution of NaHCO3 (200 mL), water (200 mL) and brine (200 mL). It was dried over MgSO4, filtered off and concentrated under vacuum giving a brown oil. It was purified by flash chromatography (cHex/EtOAc 9:1 ), affording the title compound as a colorless oil (4.38 g, 80%). 1H NMR: (DMSO-d6, 300 MHz) delta 7.94 (s, 1 H), 7.89-7.86 (dd, J = 8.06 Hz, J = 1.61 Hz, 1 H), 7.51-7.46 (m, 1 H), 7.34-7.31 (d, J = 8.13 Hz, 1 H), 7.21 -7.09 (m, 3H), 3.95 (s, 3H), 3.79 (s, 3H), 2.19 (s, 3H). LC/MS (Method A): 257.0 (M+H)+. HPLC (Method A) Rt 4.85 min (Purity: 98.9%).
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl 4-bromo-3-methylbenzoate, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; MERCK SERONO S.A.; WO2009/43889; (2009); A2;,
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