N-bromobutanimide → Methyl 2-(bromomethyl)-3-nitrobenzoate

HRID 2114186Notes

Reaction equation

HRID 2114186 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1[CH3:13].[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1[CH2:13][Br:15]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 601165Methyl 2-methyl-3-nitrobenzoate

Product 1

HCID 1487795Methyl 2-(bromomethyl)-3-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

2-Methyl-3-nitrobenzoic acid methyl ester (commercially available) is treated in a solvent such as carbon tetrachloride with N-bromosuccinimide under light to produce 2-bromomethyl-3-nitrobenzoic acid methyl ester. This benzylic bromide is treated in a solvent such as dimethylformamide with [2-(3-amino-2,6-dioxo-piperidin-1-yl)-ethyl]-phosphonic acid diethyl ester (for the preparation of this compound, see below) in the presence of a base such as triethylamine. The coupled product is then reduced by hydrogenation (Bioorg. Med. Chem. Lett., 1999, 9, 1625) to afford the desired analog.

Sources & evidence

ORD record
ord-7ac23e3f75034eb0bd6c8a40e1f32fd7
Source dataset
uspto-grants-2008_10
Patent number
US07432261B2

Reaction notes

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