Methyl 3-nitrobenzoate

A. Methyl 2-bromomethyl-3-nitrobenzoate. To a 250-mL, two-necked, round-bottomed flask, equipped with a condenser and addition funnel, is added methyl 2-methyl-3-nitrobenzoate (19.1 g, 97.9 mmol, (Note 1)), dibenzoyl peroxide (1.21 g, 5.00 mmol, (Note 2)), and 100 mL of carbon tetrachloride (Note 3). The mixture is heated to reflux, and a clear, pale yellow solution is formed. A solution of bromine (16.1 g, 100.6 mmol) (Note 2) in 20 mL of carbon tetrachloride is added over 10 min to the boiling solution under irradiation using a 100-W flood lamp. The reaction mixture is heated and irradiated for 24 hr. The resulting orange solution is allowed to cool to ambient temperature 50 mL of dichloromethane is added, and the solution is washed with three 50-mL portions of saturated aqueous sodium bicarbonate. The organic phase is dried (MgS04), filtered, and the solvents are removed at water aspirator pressure on a rotary evaporator affording 25.90 g (96.5%) of methyl 2-bromomethyl-3-nitrobenzoate as pale yellow crystals. The material is used in the next step without further purification (Note 4). 

C8H7F30 2-(trifluoromethyl)ben2yl alcohol 346-06-5 420.40 36.292 2 13186 C8H7N04 2-methyl-3-nitrobenzoic acid 1975-50-4 537.15 47.465 2... 

Methyl-3-nitrobenzoic acid, 122 4-Methyloxazole, 270 Methyl y-oxocarboxylates, 415-416 N-Methyl-N-phenylaminoacetylene,... 

Synonyms 3-Nitrobenzoic acid methyl ester Methyl 3-nitrobenzoate Source Chang, H. Morrell, D. G. 

Methyl-3-nitrobenzoic acid (3-nitro-p-toIuic acid) [96-98-0] M 181.2, m 190-191 , pK 3.62 (1% aqueous EtOH). Recrystallise the acid from EtOH. The S-benzylisothiuronium salt has m 167-168° (EtOH). The acid chloride [10397-30-5] has m 20-21°, b 185°/36mm, and the methyl ester [7356-11-8] crystallises as pale yellow needles from MeOH with m 51°. Beilstein 9 H 502, 9 II 334,9 III 2359.]... 

Bromo-(or 4-Hydroxy)methyl-3-nitrobenzoic Cleavage Product after cleavage ... 

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