Dimethyl Sulfoxide → 5-Bromo-2-methoxymethoxybenzyl cyanide

HRID 862058Notes

Reaction equation

HRID 862058 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][O:12][CH3:13])=[C:6]([CH:9]=1)[CH2:7]Cl.[C-:14]#[N:15].[Na+].ClCCl.CS(C)=O>O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][O:12][CH3:13])=[C:6]([CH:9]=1)[CH2:7][C:14]#[N:15]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6344DichloromethaneHCID 8929Sodium CyanideHCID 19701607HCID 19701607, compound

Product 1

HCID 197016225-Bromo-2-methoxymethoxybenzyl cyanideYield 97.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 5-bromo-2-methoxymethoxybenzyl chloride (21.6 g), sodium cyanide (8.33 g) and dichloromethane (10 ml) was added, at 15° to 20° C., DMSO (80 ml), followed by stirring for 3 hours at room temperature. The mixture was poured into water, which was subjected to extraction with ethyl acetate. The extract solution was washed with water, dried (anhydrous magnesium sulfate) and concentrated to leave an oily product. The oily product was purified by means of a silica gel column chromatography (eluted with ethyl acetate/hexane) to give 5-bromo-2-methoxymethoxybenzyl cyanide (20.4 g), whose spectrum data are shown below.

Workup

  1. additionwas added, at 15° to 20° C.
  2. extractionwas subjected to extraction with ethyl acetate
  3. washThe extract solution was washed with water
  4. dry with materialdried (anhydrous magnesium sulfate)
  5. concentrationconcentrated
  6. customto leave an oily product
  7. customThe oily product was purified by means of a silica gel column chromatography (eluted with ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4e6a915d2a62482e88f70474215415b4
Source dataset
uspto-grants-1998_02
Patent number
US05716971

Reaction notes

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