Phenyltrimethylammonium bromide dibromide → HCID 21520277, compound

HRID 1282831Notes

Reaction equation

HRID 1282831 reaction equation
[Br-:1].[Br-].[Br-].C[N+](C)(C)C1C=CC=CC=1.C[N+](C1C=CC=CC=1)(C)C.C[N+](C1C=CC=CC=1)(C)C.[C:34]([C:37]1[O:38][C:39]2[C:45]([CH:46]([O:48][C:49](=[O:51])[CH3:50])[CH3:47])=[CH:44][CH:43]=[CH:42][C:40]=2[CH:41]=1)(=[O:36])[CH3:35]>O1CCCC1>[C:49]([O:48][CH:46]([C:45]1[C:39]2[O:38][C:37]([C:34](=[O:36])[CH2:35][Br:1])=[CH:41][C:40]=2[CH:42]=[CH:43][CH:44]=1)[CH3:47])(=[O:51])[CH3:50]

Participants

4

Reactant 2

HCID 17977687Phenyltrimethylammonium bromide dibromideHCID 21520275HCID 21520275, compound

Product 1

HCID 21520277HCID 21520277, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

25.1 g of trimethylphenylammonium tribromide were added at 20°-25°C to a stirred solution of 16.4 g of 2-acetyl-7-(1'-acetoxyethyl)benzofuran in 250 ml of dry tetrahydrofuran. The resulting solution was stirred for 6 hours in order to complete the precipitation of trimethylphenylammonium monobromide. The mixture was poured into 1000 ml of water to which sodium chloride was added to saturation. The product was extracted with diethyl ether, the combined diethyl ether extracts were washed with water and with brine and dried over anhydrous sodium sulphate. The sodium sulphate was filtered off and the filtrate evaporated to dryness. The residual solid was crystallized from diethyl ether to give 8.7 g of 7-(1'-acetoxyethyl)-2-bromoacetylbenzofuran in the form of pale yellow crystals of melting point 86°-88°C.

Workup

  1. customthe precipitation of trimethylphenylammonium monobromide
  2. additionThe mixture was poured into 1000 ml of water to which sodium chloride
  3. additionwas added to saturation
  4. extractionThe product was extracted with diethyl ether
  5. washthe combined diethyl ether extracts were washed with water and with brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. filtrationThe sodium sulphate was filtered off
  8. customthe filtrate evaporated to dryness
  9. customThe residual solid was crystallized from diethyl ether

Sources & evidence

ORD record
ord-f7d8f9a172304ca69c889062e4db01ac
Source dataset
uspto-grants-1976_08
Patent number
US03972900

Reaction notes

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