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

HRID 1781863

Reaction equation

HRID 1781863 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3.48 g of 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 of 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°.

Workup

  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

Sources & evidence

ORD record
ord-c78ed60ce4d4418a8dcb40009c1e999f
Source dataset
uspto-grants-1997_05
Patent number
US05633371

Linked notes

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