Phenyltrimethylammonium bromide dibromide → HCID 86753719, compound

HRID 362270Notes

Reaction equation

HRID 362270 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:37]1[C:38]2[CH:45]=[C:44]([C:46]#[N:47])[CH:43]=[CH:42][C:39]=2[S:40][CH:41]=1)(=[O:36])[CH3:35]>O1CCCC1>[Br:1][CH2:35][C:34]([C:37]1[C:38]2[CH:45]=[C:44]([C:46]#[N:47])[CH:43]=[CH:42][C:39]=2[S:40][CH:41]=1)=[O:36]

Participants

4

Reactant 2

HCID 17977687Phenyltrimethylammonium bromide dibromideHCID 70283864HCID 70283864, compound

Product 1

HCID 86753719HCID 86753719, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of phenyltrimethylammonium tribromide (2.8 g) in tetrahydrofuran (5 ml) was added dropwise under nitrogen over 30 minutes to a stirred solution of 3-acetylbenzo[b]thiophen-5-carbonitrile (1.5 g) in tetrahydrofuran (50 ml), then the mixture was stirred at ambient temperature for 2 hours. The resulting solid was collected by filtration and triturated with a hot mixture of ethanol (21 ml) and acetic acid (14 ml). The product was collected by filtration and dried in vacuo to give 3-(bromoacetyl)benzo[b]thiophen-5-carbonitrile as a white solid (1.05 g).

Workup

  1. filtrationThe resulting solid was collected by filtration
  2. customtriturated with a hot mixture of ethanol (21 ml) and acetic acid (14 ml)
  3. filtrationThe product was collected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-dde8066f50f9471f8d6eefb5c22f3c3b
Source dataset
uspto-grants-1999_02
Patent number
US05869492

Reaction notes

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