Methyl 3-(broMoMethyl)-2-nitrobenzoate

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CAS:132874-06-7
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Methyl 3-(broMoMethyl)-2-nitrobenzoate manufacturers

Methyl 3-(broMoMethyl)-2-nitrobenzoate Basic information
Product Name:Methyl 3-(broMoMethyl)-2-nitrobenzoate
Synonyms:Methyl 3-(broMoMethyl)-2-nitrobenzoate;3-Bromomethyl-2-nitro-benzoic acid methyl ester;Benzoic acid, 3-(bromomethyl)-2-nitro-, methyl ester;2-Nitro-3-bromomethylbenzoic acid methyl ester
CAS:132874-06-7
MF:C9H8BrNO4
MW:274.07
EINECS:
Product Categories:
Mol File:132874-06-7.mol
Methyl 3-(broMoMethyl)-2-nitrobenzoate Structure
Methyl 3-(broMoMethyl)-2-nitrobenzoate Chemical Properties
Boiling point 349.8±32.0 °C(Predicted)
density 1.624±0.06 g/cm3(Predicted)
storage temp. Storage temp. 2-8°C
AppearanceWhite to off-white Solid
Safety Information
MSDS Information
Methyl 3-(broMoMethyl)-2-nitrobenzoate Usage And Synthesis
Synthesis
Methyl 3-methyl-2-nitrobenzoate

5471-82-9

Methyl 3-(broMoMethyl)-2-nitrobenzoate

132874-06-7

Step B: Synthesis of methyl 3-(bromomethyl)-2-nitrobenzoate; A mixture of methyl 3-methyl-2-nitrobenzoate (12.34 g, 63.23 mmol), benzoyl peroxide (0.920 g, 3.80 mmol) and N-bromosuccinimide (11.25 g, 63.21 mmol) in carbon tetrachloride (330 mL) was heated at refluxed for 12 h. The reaction was carried out under nitrogen protection. Upon completion of the reaction, the cooled mixture was diluted with dichloromethane (150 mL), treated with silica gel (30 g) and the solvent was removed under reduced pressure. The residue was purified by fast column chromatography on silica gel using ethyl acetate/hexane (15:85) as eluent to afford methyl 3-(bromomethyl)-2-nitrobenzoate (1B) as a light yellow solid (7.15 g, 41% yield). The product was confirmed by 1H NMR (CDCl3): δ 3.91 (s, 3H), 4.46 (s, 2H), 7.58 (t, 1H), 7.74 (dd, 1H), 7.96 (dd, 1H).

References[1] Organic and Biomolecular Chemistry, 2014, vol. 12, # 30, p. 5629 - 5633
[2] Organic Process Research and Development, 2011, vol. 15, # 4, p. 831 - 840
[3] Journal of Organic Chemistry, 1997, vol. 62, # 17, p. 5838 - 5845
[4] Tetrahedron, 2004, vol. 60, # 10, p. 2235 - 2246
[5] Patent: WO2005/66136, 2005, A1. Location in patent: Page/Page column 88
Methyl 3-(broMoMethyl)-2-nitrobenzoate Preparation Products And Raw materials
Raw materialsMethyl 3-methyl-2-nitrobenzoate-->Perbenzoic acid-->Carbon tetrachloride-->N-Bromosuccinimide
Preparation ProductsMethyl 3-formyl-2-nitrobenzoate
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