Triethylamine → 2-(2-Bromomethyl-benzyloxy)-isoindole-1,3-dione

HRID 1582292

반응식

HRID 1582292 반응식
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].CCN(CC)CC.[Br:20][CH2:21][C:22]1[C:23]([CH2:28]Br)=[CH:24][CH:25]=[CH:26][CH:27]=1>CN(C=O)C>[Br:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH2:28][O:1][N:2]1[C:3](=[O:12])[C:4]2[C:5](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:7]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 10665N-HydroxyphthalimideHCID 66665o-Bis(bromomethyl)benzene

생성물 1

HCID 219851622-(2-Bromomethyl-benzyloxy)-isoindole-1,3-dione수율 46%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of N-hydroxyphthalimide (0.60 g, 3.68 mmol) and Et3N (0.60 mL, 4.30 mmol) in DMF (6 mL) was added α,α′-dibromo-o-xylene (3.30 g, 0.0125 mol) and the mixture stirred at room temperature for 4 h. The resultant brown precipitate was filtered and washed with CH2Cl2. The filtrate was diluted with EtOAc (40 mL) and water (30 mL) and the organic phase washed with brine (1×30 mL), dried (Na2SO4) and concentrated under reduced pressure. The resultant yellow oil was purified by column chromatography on silica gel (4:1 Hexanes/EtOAc) to give the title compound (581 mg, 46%) as a white solid. 1H NMR (CDCl3) δ4.99 (s, 2H), 5.37 (s, 2H), 7.27-7.40 (m, 2H), 7.41-7.45 (m, 2H), 7.73-7.76 (m, 2H), 7.81-7.84 (m, 2H).

후처리

  1. filtrationThe resultant brown precipitate was filtered
  2. washwashed with CH2Cl2
  3. additionThe filtrate was diluted with EtOAc (40 mL) and water (30 mL)
  4. washthe organic phase washed with brine (1×30 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe resultant yellow oil was purified by column chromatography on silica gel (4:1 Hexanes/EtOAc)

출처 및 근거

ORD 기록
ord-e1ba1fd89c434498a655f168340c1bc8
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06734191B2

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