Sodium periodate → 3-Chloro-4-formylbenzonitrile

HRID 2090198Notes

Reaction equation

HRID 2090198 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH:10]=CN(C)C)[C:5]#[N:6].I([O-])(=O)(=O)=[O:16].[Na+]>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH:10]=[O:16])[C:5]#[N:6]

Participants

4

Reactant 2

HCID 23667635Sodium periodateHCID 873920413-Chloro-4-[2-(dimethylamino)vinyl]benzonitrile

Product 1

HCID 122905503-Chloro-4-formylbenzonitrile

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

The crude 3-chloro-4-[2-(dimethylamino)vinyl]benzonitrile obtained in this way is taken up in 500 ml of THF/water (1:1), and 77.6 g (362.9 mmol) of sodium periodate are added. The mixture is stirred at room temperature for 18 h, and then the precipitate which has separated out is removed by filtration. The filtrate is mixed with saturated sodium bicarbonate solution and extracted three times with ethyl acetate. The combined organic phases are dried with sodium sulfate, and the solvent is removed in a rotary evaporator. The crude product is purified by column chromatography (silica gel, mobile phase: cyclohexane/ethyl acetate 7:3). 3.0 g (15% of theory) of the title compound are obtained.

Workup

  1. customthe precipitate which has separated out
  2. customis removed by filtration
  3. additionThe filtrate is mixed with saturated sodium bicarbonate solution
  4. extractionextracted three times with ethyl acetate
  5. dry with materialThe combined organic phases are dried with sodium sulfate
  6. customthe solvent is removed in a rotary evaporator
  7. customThe crude product is purified by column chromatography (silica gel, mobile phase: cyclohexane/ethyl acetate 7:3)

Sources & evidence

ORD record
ord-d16e1e8c34f34d2a94c5d8ca2434f704
Source dataset
uspto-grants-2013_05
Patent number
US08436180B2

Reaction notes

Loading…