1-Bromopentane → HCID 12343242, compound

HRID 540391Notes

Reaction equation

HRID 540391 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:9]#[N:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 80571-BromopentaneHCID 24758Sodium hydrideHCID 68016Benzeneacetonitrile, 4-fluoro-

Product 1

HCID 12343242HCID 12343242, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

5 g (37.0 mmol) of (4-fluorophenyl)acetonitrile are added dropwise to a suspension of 1.62 g of 60% NaH in 50 ml of DMF cooled to 0° C. After stirring for 30 minutes at 0° C., 4.62 mmol (37.0 mmol) of bromopentane are added dropwise. The reaction medium is stirred for 16 hours at ambient temperature and then treated with ice and extracted with dichloromethane. The organic phase is dried over sodium sulphate, filtered and evaporated under pressure. An orangey-yellow oil is obtained and used as it is in the next stage.

Workup

  1. stirringThe reaction medium is stirred for 16 hours at ambient temperature
  2. additiontreated with ice
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic phase is dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated under pressure
  7. customAn orangey-yellow oil is obtained

Sources & evidence

ORD record
ord-3d91fa5f8f9b4bacacd7634ec950a474
Source dataset
uspto-grants-2014_10
Patent number
US08871187B2

Reaction notes

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