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

HRID 390585

반응식

HRID 390585 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 21226129Dichloromethane methanol용매

실험 절차

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-dimethylaminomethyl pyridine (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.

출처 및 근거

ORD 기록
ord-ed0281c5bc0e43838b727eaf5f033ed9
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383662B2

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