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N-bromobutanimide → Methyl 4-(bromomethyl)-2-methoxybenzoate

HRID 59314
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HRID 59314 반응식
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].C1C(=O)N([Br:21])C(=O)C1>C(Cl)(Cl)(Cl)Cl.C(OCC)C.CC(N=NC(C#N)(C)C)(C#N)C>[Br:21][CH2:13][C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[C:3]([O:2][CH3:1])[CH:12]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 2

HCID 67184N-bromobutanimideHCID 7172021Methyl 2-methoxy-4-methylbenzoate

생성물 1

HCID 11288398Methyl 4-(bromomethyl)-2-methoxybenzoate수율 70.2%

시약·촉매·용매 3

HCID 6547Azobisisobutyronitrile촉매HCID 3283Diethyl Ether용매HCID 5943Carbon Tetrachloride
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실험 절차

To a solution of methyl 2-methoxy-4-methylbenzoate (10.00 g, 55 mmol) in CCl4 (150 mL) were added NBS (11.8 g, 66 mmol) and AIBN (0.100 g). The reaction mixture was refluxed for 18 h. The reaction mass was diluted with diethyl ether and washed with 25% NaOH solution. The organic layer was dried over anhydrous sodium sulphate and concentrated to afford 10.00 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 3.77 (m, 6H), 4.68 (s, 2H), 7.06 (d, J=7.8 Hz, 1H), 7.23 (s, 1H), 7.61 (d, J=7.8 Hz, 1H); MS (m/z): 259.13 (M)+.

후처리

  1. temperatureThe reaction mixture was refluxed for 18 h
  2. washwashed with 25% NaOH solution
  3. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-6d9a70ba4d3d4031a7a8f9ca00e906c1
출처 데이터셋
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09439890B2

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