Dicyclohexylcarbodiimide → Methyl 4-(bromomethyl)-3-nitrobenzoate

HRID 1170255Notes

Reaction equation

HRID 1170255 reaction equation
[CH:1]1(N=C=NC2CCCCC2)CCCCC1.[Br:16][CH2:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][C:19]=1[N+:27]([O-:29])=[O:28].CN(CC1C=CN=CC=1)C>ClCCl.ClCCl.CO>[CH3:1][O:23][C:22](=[O:24])[C:21]1[CH:25]=[CH:26][C:18]([CH2:17][Br:16])=[C:19]([N+:27]([O-:29])=[O:28])[CH:20]=1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 1323864-Bromomethyl-3-nitrobenzoic acidHCID 2649464-pyridinemethanamine, N,N-dimethyl-

Product 1

HCID 13399987Methyl 4-(bromomethyl)-3-nitrobenzoate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of dicyclohexylcarbodiimide (DCC, 0.95 g, 4.61 mmol, 1.2 equiv) in 10 mL of dichloromethane (DCM) was added dropwise to a stirred mixture of 4-bromomethyl-3-nitro-benzoic acid 1 (1.0 g, 3.84 mmol, 1.0 equiv) and 4-dimethylaminomethylpyridine (DMAP) (0.020 g, 0.19 mmol, 0.05 equiv) in 10 mL of dichloromethane-methanol (10%) at room temperature. The mixture was stirred for 6 hours to obtain 4-bromomethyl-3-nitro-benzoic acid methyl ester 2. Dicyclohexyl urea (DCU) thus obtained was removed by filtration and the solvent in the filtered solution was removed under vacuum. The residue was purified by column chromatography using hexane-ethyl acetate (15%) as an eluant to give ester 2 as a light yellow oil.

Sources & evidence

ORD record
ord-b2ed8b5eb7294125b0663e5aa2c912fc
Source dataset
uspto-grants-2010_11
Patent number
US07825261B2

Reaction notes

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