Benzoyl Peroxide → Methyl 2-(4-methoxybenzyl)isoindoline-5-carboxylate

HRID 508570

반응식

HRID 508570 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6].BrN1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(N(CC)CC)C.[CH3:46][O:47][C:48]1[CH:55]=[CH:54][C:51]([CH2:52][NH2:53])=[CH:50][CH:49]=1>C(Cl)(Cl)(Cl)Cl.C1COCC1>[CH3:46][O:47][C:48]1[CH:55]=[CH:54][C:51]([CH2:52][N:53]2[CH2:1][C:2]3[C:11](=[CH:10][CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:3]=3)[CH2:12]2)=[CH:50][CH:49]=1

참가 물질

8

반응물 5

HCID 7187Benzoyl PeroxideHCID 8471TriethylamineHCID 67184N-bromobutanimideHCID 754524-MethoxybenzylamineHCID 520902Methyl 3,4-dimethylbenzoate

생성물 1

HCID 58147238Methyl 2-(4-methoxybenzyl)isoindoline-5-carboxylate수율 49%

시약·촉매·용매 2

HCID 5943Carbon Tetrachloride용매HCID 8028Tetrahydrofuran용매2회

실험 절차

A mixture of methyl 3,4-dimethylbenzoate (1.334 g, 8.13 mmol), N-bromosuccinimide (3.173 g, 17.83 mmol) and benzoyl peroxide (0.143 g, 0.592 mmol) in carbon tetrachloride (5 mL) was heated at reflux for 1.5 hours. Upon cooling to room temperature, the solids present were removed by vacuum filtration and the resulting solution concentrated in vacuo. The residue obtained was re-dissolved in THF (30 mL). To the solution was added triethylamine (2.265 mL, 16.25 mmol) and a solution of 4-methoxy benzylamine (1.05 mL, 8.13 mmol) in THF (20 mL). The resulting reaction mixture was stirred overnight at room temperature. The precipitate was removed via filtration and the solution obtained was concentrated in vacuo. The residue obtained was purified via flash chromatography (15-30% EtOAc/hexane) to afford a light yellow oil (1.185 g). LCMS: (FA) ES+ 298; 1H NMR (CDCl3, 400 MHz) 7.89 (dd, J=7.8, 1.5 Hz, 1H), 7.84 (s, 1H), 8.74 (d, J=8.7 Hz, 2H), 7.313 (d, J=8.7 Hz 2H), 7.22 (d, J=7.2 Hz, 2H), 6.89 (d, J=8.7 Hz, 2H), 3.93 (s, 4H), 3.89 (s, 3H), 3.85 (s, 2H), 3.82 (s, 3H).

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 hours
  3. customthe solids present were removed by vacuum filtration
  4. concentrationthe resulting solution concentrated in vacuo
  5. customThe residue obtained
  6. customThe resulting reaction mixture
  7. customThe precipitate was removed via filtration
  8. customthe solution obtained
  9. concentrationwas concentrated in vacuo
  10. customThe residue obtained
  11. customwas purified via flash chromatography (15-30% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-ce547ad2ccab415eb87838eb9c7a6cec
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096518B2

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