4-Bromobutyronitrile → HCID 53826452, compound

HRID 1634105Notes

Reaction equation

HRID 1634105 reaction equation
[I:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](O)=[CH:7]2.[CH3:13][CH2:14][O-:15].[Na+].BrCC[CH2:20][C:21]#[N:22]>CCO.O>[C:21]([CH2:20][CH2:13][CH2:14][O:15][C:7]1[C:8]2[C:3](=[C:2]([I:1])[CH:11]=[CH:10][CH:9]=2)[CH:4]=[CH:5][CH:6]=1)#[N:22]

Participants

6

Reactant 3

HCID 214124-BromobutyronitrileHCID 2723922Sodium ethoxideHCID 186771115-Iodonaphthalen-2-ol

Product 1

HCID 53826452HCID 53826452, compoundYield 20.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred mixture of 5-iodo-2-naphthol (300 mg, 1.11 mmol) in EtOH (7 mL) was added NaOC2H5 (90.7 mg, 1.2 equiv) and, after 10 min, 4-bromobutyronitrile (0.22 mL, 2.0 equiv). The mixture was then heated at reflux for 2 h. It was diluted with water, extracted with dichloromethane, washed with brine and dried (Na2SO4). Concentration and chromatography on silica gel (hexane/ethyl acetate=4:1) gave 1-(cyanopropyloxy)-5-iodonaphthalene (77 mg, 20.6%).

Workup

  1. temperatureThe mixture was then heated
  2. temperatureat reflux for 2 h
  3. extractionextracted with dichloromethane
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationConcentration and chromatography on silica gel (hexane/ethyl acetate=4:1)

Sources & evidence

ORD record
ord-b1666321f20049129c5f305b524a87c9
Source dataset
uspto-grants-2003_01
Patent number
US06506747B1

Reaction notes

Loading…