4-BROMO-3-BROMOMETHYL-BENZOIC ACID METHYL ESTER

Step 1:; Preparation of Methyl 4-bromo-3-bromomethylbenzoate In a 6-liter reactor equipped with a condenser, a central mechanical stirrer and a thermometer, introduce 575 g (2.5 mol) of methyl 4-bromo-3-methylbenzoate, 3 liters of methylene chloride, 494 g (2.75 mol) of N-bromosuccinimide and 17 g of benzoyl peroxide (0.05 mol; 70percent in water). Heat the mixture at reflux under irradiation with a 1000 watt lamp for 10 h. Wash the mixture twice with 1 liter of water, then with 1 liter of saturated sodium chloride solution. Evaporate the methylene chloride. Recrystallize the crude product obtained from heptane. This gives 596 g of methyl 4-bromo-3-bromomethylbenzoate in the form of off-white crystals (Yield=77percent) Melting point: 100-101° C. Method 10D: using the appropriate methyl benzoate.Free-Radical Bromination of MethylbenzeneA solution of methylbenzene (1eq), N_bromosuccinimide (1.1eq), and benzoyle peroxide (0.01eq) in dichloromethane was stirred at reflux under irradiation of a 75W lamp for 24 hours. The reaction mixture was washed with water, then with brine. The organic layer was dried over magnesium sulfate, filtered and evaporated under reduced pressure. The product was purified by recristallization.10.6.1 26e) methyl 4-bromo-3-(bromomethyl)benzoateA solution of methyl 4-bromo-3-methylbenzoate (20.0 g, 87.3 mmol), N- bromosuccinimide (18.7 g, 105 mmol), 1 , i '-azobis(cyclohexanecarbonitrile) (0.5 g) in acetonitrile (100 mL) was heated at reflux for 12 h. This was cooled EPO Methyl 4-bromo-3-methylbenzoate (11.4 g, 0.05 mol) was added to carbon tetrachloride (80 mL) in a 250 mL 3-three neck round-bottomed flask. To a solution of methyl 4-bromo-3-methylbenzoate (5.0 g, 21.83 mmol) in carbon tetrachloride (120 mL) was added NBS (4.67 g, 26.20 mmol), the suspension was heated at 80 °C for 5 min. Then AIBN (1.79 g, 10.92 mmol) was added. The suspension was stirred at 80 °C for 16 h. The reaction was cooled to RT and filtered. The filtrate was concentrated and purified by silica gel chromatography eluting with EA/petroleum ether from 0percent to 3percent to give methyl 4-bromo-3-(bromomethyl)benzoate (4.12 g, 61.5percent) as a white solid.Preparation 23: methyl 4-bromo-3-(bromomethyl)benzoateTo a CClStep 1 Methyl 4-bromo-3-(bromomethyl)benzoate Methyl 4-bromo-3-(bromomethyl)benzoate

Molecular Weight:307.97
XLogP3:3
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:307.88706
Monoisotopic Mass:305.88910
Topological Polar Surface Area:26.3
Heavy Atom Count:13
Complexity:185
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes