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Azobisisobutyronitrile → Tert-butyl 2-(5-(bromomethyl)-2-(methoxymethoxy)benzamido)-4-phenylbenzoate

HRID 454642
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HRID 454642 반응식
[Br:1]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.[CH3:21][O:22][CH2:23][O:24][C:25]1[CH:52]=[CH:51][C:50]([CH3:53])=[CH:49][C:26]=1[C:27]([NH:29][C:30]1[CH:42]=[C:41]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:40]=[CH:39][C:31]=1[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[O:28].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.C1C=CC=CC=1>[Br:1][CH2:53][C:50]1[CH:51]=[CH:52][C:25]([O:24][CH2:23][O:22][CH3:21])=[C:26]([CH:49]=1)[C:27]([NH:29][C:30]1[CH:42]=[C:41]([C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH:40]=[CH:39][C:31]=1[C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[O:28]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 66991033Tert-butyl 2-(2-(methoxymethoxy)-5-methylbenzamido)-4-phenylbenzoate

생성물 1

HCID 66990849Tert-butyl 2-(5-(bromomethyl)-2-(methoxymethoxy)benzamido)-4-phenylbenzoate수율 69%

시약·촉매·용매 2

HCID 241
Benzene
용매
HCID 8857Ethyl Acetate용매

실험 절차

N-Bromosuccinimide (0.25 g) and azobisisobutyronitrile (0.023 g) were sequentially added to a benzene (6.3 mL) solution of the obtained tert-butyl 2-(2-(methoxymethoxy)-5-methylbenzamido)-4-phenylbenzoate (0.63 g), followed by heating to reflux for 30 minutes. The reaction mixture was cooled to room temperature, and then a saturated aqueous solution of sodium bicarbonate and ethyl acetate were added thereto. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 100-90% hexane/ethyl acetate] to obtain 0.51 g of tert-butyl 2-(5-(bromomethyl)-2-(methoxymethoxy)benzamido)-4-phenylbenzoate as a white solid.

후처리

  1. temperatureby heating
  2. temperatureto reflux for 30 minutes
  3. customThe organic layer was separated
  4. washwashed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography [eluent: 100-90% hexane/ethyl acetate]

출처 및 근거

ORD 기록
ord-d6d0d66f761840ceb7c843bcb2689d3b
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08492582B2

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