ChemicalBook CAS DataBase List Methyl 2-bromomethyl-3-nitrobenzoate

Methyl 2-bromomethyl-3-nitrobenzoate synthesis

4synthesis methods

Product Name:Methyl 2-bromomethyl-3-nitrobenzoate
CAS Number:98475-07-1
Molecular formula:C9H8BrNO4
Molecular Weight:274.07

Methyl 2-bromomethyl-3-nitrobenzoate can be used as organic synthesis intermediates and pharmaceutical intermediates, mainly used in laboratory research and development processes. A solution of methyl 2-methyl-3-nitrobenzoate in carbon tetrachloride is stirred under reflux,N-bromosuccinimide and 2,2'-azobis-2-methylpropanenitrile are added and the mixture is stirred under reflux overnight to give Methyl 2-bromomethyl-3-nitrobenzoate.

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Yield:98475-07-1 100%

Reaction Conditions:

with N-Bromosuccinimide;2,2'-azobis(isobutyronitrile) in tetrachloromethaneReflux;

Steps:

9A.a
Step a) Methyl 2-(bromomethyl)-3-nitrobenzoate A solution of 21 g (109 mmol) of methyl 2-methyl-3-nitrobenzoate in 300 ml of carbon tetrachloride is stirred under reflux, 23 g (130 mmol, 1.2 eq.) of N-bromosuccinimide and 1.8 g (11 mmol, 0.1 eq.) of 2,2'-azobis-2-methylpropanenitrile are added and the mixture is stirred under reflux overnight. After cooling to RT, the reaction mixture is diluted with dichloromethane, washed repeatedly with water, dried over sodium sulphate, filtered and concentrated under reduced pressure.Yield: 31 g (quantitative)HPLC (Method 12): R_t=4.33 min;MS (ESIpos): m/z=273 [M+H]⁺;¹H-NMR (300 MHz, DMSO-d₆): δ=8.16 (d, 1H), 8.11 (d, 1H), 7.74 (t, 1H), 5.03 (s, 2H), 3.92 (s, 3H).

References:

Bayer Healthcare AG US2010/10060, 2010, A1 Location in patent:Page/Page column 19

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