Water → 2,3,4-Trimethoxyphenylacetonitrile

HRID 1861578Notes

Reaction equation

HRID 1861578 reaction equation
C(Br)C1C=CC=CC=1.Br[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[C:12]=1[O:21][CH3:22].[C-:23]#[N:24].[K+].O>CN(C=O)C>[CH3:22][O:21][C:12]1[C:13]([O:19][CH3:20])=[C:14]([O:17][CH3:18])[CH:15]=[CH:16][C:11]=1[CH2:10][C:23]#[N:24]

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 9032Potassium CyanideHCID 134493141-(Bromomethyl)-2,3,4-trimethoxybenzene

Product 1

HCID 1443172,3,4-Trimethoxyphenylacetonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Phosphortribromide (6.83 g, 25.22 mmol) was added dropwise to a stirred solution of 2,3,4-trimethoxybenzyl alcohol (10 g, 54.44 mmol) in dichloromethane (100 ml), cooled at 0° C. After 30 min of vigorous stirring, the reaction mixture was slowly quenched with 100 g of ice-water. The dichloromethane layer was separated and the aqueous layer was further extracted with dichloromethane (2×100 ml). The combined extracts were twice washed with a saturated solution of sodium chloride (2×150 ml). The organic solution was dried over magnesium sulphate and evaporated to give 10 g (yield 76%) of the benzylbromide 2 as a colourless oil. As soon as isolated, the benzyl bromide compound was directly used for the next step. In fact the compound degradated after one night even at +4° C. The obtained 1-bromomethyl-2,3,4-trimethoxybenzene oil was treated with KCN (6.52 g, 100 mmol) in dry DMF (30 ml), at 0° C. and under nitrogen atmosphere. The obtained mixture was stirred for 3 g at 0° C. and 1 h at 60° C. The cooled reaction mixture was poured into water (80 ml) and extracted with diethylether (3×150 ml). The crude benzylcyanid was chromatographed on silica (diethylether/petroleumether: 1/3) to give 2,3,4-trimethoxyphenyl-acetonitrile as a white crystalline material (Yield: 6.8 g; 86%).

Workup

  1. customAs soon as isolated
  2. waitIn fact the compound degradated after one night even at +4° C
  3. customThe cooled reaction mixture
  4. extractionextracted with diethylether (3×150 ml)
  5. customThe crude benzylcyanid was chromatographed on silica (diethylether/petroleumether: 1/3)

Sources & evidence

ORD record
ord-4a7439613f994ac9ba2dde02fac02c60
Source dataset
uspto-grants-2003_03
Patent number
US06534135B1

Reaction notes

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