Water → HCID 70136055, compound

HRID 1419494Notes

Reaction equation

HRID 1419494 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([C:7]([C:9]2[C:10]([Cl:17])=[C:11]([CH:14]=[CH:15][CH:16]=2)[CH2:12]Br)=[O:8])=[CH:5][CH:4]=1.[C-:20]#[N:21].[K+].O>CS(C)=O>[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([C:7]([C:9]2[C:10]([Cl:17])=[C:11]([CH2:12][C:20]#[N:21])[CH:14]=[CH:15][CH:16]=2)=[O:8])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 9032Potassium CyanideHCID 53881843HCID 53881843, compound

Product 1

HCID 70136055HCID 70136055, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

3-(4-Methoxybenzoyl)-2-chlorotoluene (4.55 g, 17.45 mmol) [prepared by the method described in Example 1(a)]was dissolved in benzene (150 ml), and the solution was purged with nitrogen. N-Bromosuccinimide (3.10 g, 1 eq.) and benzoyl peroxide (0.42 g, 0.1 eq.) were added and the reaction mixture was heated at reflux overnight. Since there was an appreciable amount of unreacted starting material still present in the reaction mixture, additional amounts of N-bromosuccinimide (1.55 g, 0.5 eq.) and benzoyl peroxide (0.21 g, 0.05 eq.) were added, and the heating was continued. After 3 h the reaction mixture was cooled to room temperature, and diluted with ether. The organic layer was separated, washed with water and brine, and dried over MgSO4. The solvent was removed in vacuo to give 7.6 g of an orange oil. Purification by flash chromatography (10/90 EtOAc/hexanes) gave 3-(4-methoxybenzoyl)-2-chlorobenzyl bromide as an oil that slowly crystallized to a solid (5.13 g, 87% yield). 1H NMR showed it was approximately 90% pure 3-(4-methoxybenzoyl)-2-chlorobenzyl bromide (4.97 g, 1 eq.) [prepared as described above] was added to a solution of KCN (1.05 g, 1.1 eq.) in dry DMSO (40 ml) under a nitrogen atmosphere. After 30 min the reaction mixture was poured into water (1 L) and the product was extracted into ethyl acetate. The organic extract was washed with water and brine, and dried over MgSO4. The solvent was evaporated in vacuo to give 2-[3-(4-methoxy-benzoyl)-2-chlorophenyl]acetonitrile (4.08 g, 98% yield) as an oil.

Workup

  1. extractionthe product was extracted into ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with water and brine
  4. dry with materialdried over MgSO4
  5. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-8a0858a95b874371b24320b566743e14
Source dataset
uspto-grants-1999_03
Patent number
US05886178

Reaction notes

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