Phenyltrimethylammonium bromide dibromide → HCID 21325159, compound

HRID 973244Notes

Reaction equation

HRID 973244 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([OH:13])=[C:8]([CH2:10][C:11]#[N:12])[CH:9]=1)(=[O:3])[CH3:2].[Br-:14].[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>O1CCCC1>[Br:14][CH2:2][C:1]([C:4]1[CH:5]=[CH:6][C:7]([OH:13])=[C:8]([CH2:10][C:11]#[N:12])[CH:9]=1)=[O:3]

Participants

4

Reactant 2

HCID 17977687Phenyltrimethylammonium bromide dibromideHCID 21325149HCID 21325149, compound

Product 1

HCID 21325159HCID 21325159, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 5-acetyl-2-hydroxyphenylacetonitrile (3.5 g., 0.02 mole) in 100 ml. of tetrahydrofuran is added trimethylphenylammonium tribromide (7.6 g., 0.02 mole) portionwise over a 15 min. period with stirring. After stirring for an additional 18 hrs. at 25° C., the reaction mixture is concentrated to dryness under reduced pressure. Trituration of residual material with water affords 5.0 g. of brominated product, m.p. 187°-191° C. (dec.). Crystallization of this material from isopropanol affords 5-bromoacetyl-2-hydroxyphenylacetonitrile, m.p. 196°-198° C. (dec.).

Workup

  1. stirringAfter stirring for an additional 18 hrs
  2. concentrationat 25° C., the reaction mixture is concentrated to dryness under reduced pressure
  3. customTrituration of residual material with water affords 5.0 g
  4. customCrystallization of this material from isopropanol

Sources & evidence

ORD record
ord-cd4e4d77731a4d408ceca9609abd52b2
Source dataset
uspto-grants-1977_10
Patent number
US04055658

Reaction notes

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