N-bromobutanimide → Dimethyl 4-(bromomethyl)isophthalate

HRID 1784195

반응식

HRID 1784195 반응식
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=1.[Br:16]N1C(=O)CCC1=O.N(C1(C#N)CCCCC1)=NC1(C#N)CCCCC1>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[CH:12][C:11]([CH2:14][Br:16])=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=1

참가 물질

5

반응물 3

HCID 67184N-bromobutanimideHCID 749781,1'-Azobis(cyclohexanecarbonitrile)HCID 899711,3-Benzenedicarboxylic acid, 4-methyl-, 1,3-dimethyl ester

생성물 1

HCID 14920817Dimethyl 4-(bromomethyl)isophthalate

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

4-Methyl-isophthalic acid dimethyl ester (1.06 g, 5.10 mmol), N-bromosuccinimide (1.00 g, 5.61 mmol) and 1,1′-azobis(cyclohexanecarbonitrile) (0.31 g, 1.27 mmol) were suspended in carbon tetrachloride (22 mL) and the resulting mixture was refluxed for 16 hours under N2. The orange solution was concentrated under reduced pressure and the resulting orange residue was purified via column chromatography on silica gel (hexanes:EtOAc, 7:1, v/v). 4-Bromomethyl-isophthalic acid dimethyl ester was isolated as a yellow crystalline solid (1.05 g, 72%). 1H NMR (CDCl3) δ 3.95 (s, 3H), 3.97 (s, 3H), 4.96 (s, 2H), 7.57 (d, 1H, J=9.0 Hz), 8.13 (dd, 1H, J=9.0, 3.0 Hz), 8.62 (d, 1H, J=3.0 Hz).

후처리

  1. temperaturethe resulting mixture was refluxed for 16 hours under N2
  2. concentrationThe orange solution was concentrated under reduced pressure
  3. customthe resulting orange residue was purified via column chromatography on silica gel (hexanes

출처 및 근거

ORD 기록
ord-da4dcd5cf6f748469c422da922640649
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07501518B2

연결된 노트

불러오는 중…