Water → HCID 20536257, compound

HRID 1155946Notes

Reaction equation

HRID 1155946 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][C:4]=1[CH2:5][C:6]#N.[H-].[Na+].[CH3:15]I.O.C[N:19]([CH3:22])C=O>>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][C:4]=1[C:5]([C:22]#[N:19])([CH3:15])[CH3:6]

Participants

6

Reactant 5

HCID 962WaterHCID 6228Dimethylformamide2×HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 27355805-Bromo-2-Methoxyphenylacetonitrile

Product 1

HCID 20536257HCID 20536257, compound

Procedure

2-Methoxy-5-bromobenzyl cyanide (prepared by reaction of 2-methyl-4-bromoanisole, benzoyl peroxide and bromine, followed by reaction with sodium cyanide) (47 g, 0.208 mole) in dimethyl formamide (100 ml) was added cautiously to a cooled, stirred mixture of sodium hydride 10 g (0.416 mole) and dry dimethyl formamide (500 ml). After 15 minutes, methyl iodide (59 g, 0.416 mole) was added dropwise at 15°-20° C. (external cooling) and the mixture stirred at room temperature for 21/2 hours. Water was then added very cautiously until no further reaction occurred. Addition to a large excess of ice and filtration gave after drying 49 g (92%) buff solid which was shown to be the title product by NMR.

Workup

  1. temperature(external cooling)
  2. stirringthe mixture stirred at room temperature for 21/2 hours
  3. additionAddition to a
  4. filtrationlarge excess of ice and filtration
  5. customgave
  6. customafter drying 49 g (92%) buff solid which

Sources & evidence

ORD record
ord-a27208d15346459187886049e6883d89
Source dataset
uspto-grants-1982_06
Patent number
US04333759

Reaction notes

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