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

HRID 1170255

반응식

HRID 1170255 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-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.

출처 및 근거

ORD 기록
ord-b2ed8b5eb7294125b0663e5aa2c912fc
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07825261B2

연결된 노트

불러오는 중…