Phenyltrimethylammonium bromide dibromide → 5-(Bromoacetyl)-2,3-dimethoxybenzonitrile

HRID 725372

반응식

HRID 725372 반응식
[Br-:1].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.[C:34]([C:36]1[C:37]([O:47][CH3:48])=[C:38]([O:45][CH3:46])[CH:39]=[C:40]([C:42](=[O:44])[CH3:43])[CH:41]=1)#[N:35]>O1CCCC1>[Br:1][CH2:43][C:42]([C:40]1[CH:39]=[C:38]([O:45][CH3:46])[C:37]([O:47][CH3:48])=[C:36]([CH:41]=1)[C:34]#[N:35])=[O:44]

참가 물질

4

반응물 2

HCID 17977687Phenyltrimethylammonium bromide dibromideHCID 214589805-Acetyl-2,3-dimethoxybenzonitrile

생성물 1

HCID 214589615-(Bromoacetyl)-2,3-dimethoxybenzonitrile

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

3.48 g or phenyltrimethylammonium bromide dibromide dissolved in 30 ml of tetrahydrofuran are added dropwise at room temperature within 45 minutes to 1.9 g of 5'-cyano-3',4'-dimethoxyacetophenone dissolved in 30 ml of tetrahydrofuran, whereupon the mixture is stirred for 30 minutes. Thereupon, the reaction mixture is poured into 120 ml or ice-water and extracted three times with 70 ml of methylene chloride. The combined methylene chloride phases are washed with 2N sulfuric acid, dried over sodium sulfate and evaporated. The residue is chromatographed on 20 g of silica gel with methylene chloride. After recrystallization from methylene chloride/hexane there is obtained 5-(bromoacetyl)-2,3-dimethoxybenzonitrile of m.p. 138°-141°.

후처리

  1. extractionextracted three times with 70 ml of methylene chloride
  2. washThe combined methylene chloride phases are washed with 2N sulfuric acid
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe residue is chromatographed on 20 g of silica gel with methylene chloride
  6. customAfter recrystallization from methylene chloride/hexane there

출처 및 근거

ORD 기록
ord-b01e3ed9e6a04125b26424436d788a47
출처 데이터셋
uspto-grants-1998_01
특허 번호
US05705703

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