Dichloromethane → HCID 20510030, compound

HRID 1758276Notes

Reaction equation

HRID 1758276 reaction equation
ClC[C:3]1([CH3:13])[CH:7]([CH3:8])[C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[O:4]1.[C-:14]#[N:15].[Na+].Cl[CH2:18]Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH3:13][C:3]1[O:4][C:5]2[CH:12]=[C:11]([CH2:18][C:14]#[N:15])[CH:10]=[CH:9][C:6]=2[C:7]=1[CH3:8]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 8929Sodium CyanideHCID 20510034HCID 20510034, compound

Product 1

HCID 20510030HCID 20510030, compoundYield 52.6%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent2×

Procedure

A mixture of 2-chloromethyl-2,3-dimethylbenzofuran (7.2 g, 0.037 mol), sodium cyanide (3.57 g, 0.073 mol), tetrabutylammonium bromide (0.74 g, 2.3×10-3 mol), water (19 cm3) and dichloromethane (19 cm3) was vigorously stirred for 18 hr. The mixture was poured into water and extracted with dichloromethane. The extract was washed with water, dried (Na2SO4), filtered and the solvent was removed to give 2,3-dimethylbenzofuran-6-acetonitrile (3.6 g, 0.0194 mol; 52.6%). (Found: C, 77.59; H, 6.11; N, 7.40. C2H11NO requires C, 77.81; H, 5.99; N, 7.56%) t.l.c./silica/toluene RF 0.45.

Workup

  1. extractionextracted with dichloromethane
  2. washThe extract was washed with water
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-b54e12de5bba4565af695d241f182608
Source dataset
uspto-grants-1983_02
Patent number
US04372970

Reaction notes

Loading…