Phenethyl bromide → HCID 18994297, compound

HRID 1608790Notes

Reaction equation

HRID 1608790 reaction equation
[H-].[Na+].Br[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[F:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)[C:20]#[N:21])=[CH:15][CH:14]=1>CN(C=O)C>[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)([CH2:4][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:20]#[N:21])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7666Phenethyl bromideHCID 24758Sodium hydrideHCID 67731667HCID 67731667, compound

Product 1

HCID 18994297HCID 18994297, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

In a 300 ml. 3 neck round bottomed flask under N2 was charged 0.9 g. of 60% NaH (1.5 eq., 0.0225 moles), washed 2 times with 15 ml hexanes, in 40 ml. DMF and 5.5 g. of 2-bromoethylbenzene (2.0 eq., 0.030 moles). This was followed by the addition of 3.18 g. of alpha-4-fluorophenyl-3-pyridylacetonitrile (1.0 eq., 0.015 moles) in 10 ml. DMF which resulted in an exotherm to 46° C. After 15 min. GLC analysis showed no unreacted nitrile. The reaction was quenched by the addition of 100 ml. water and then extracted with 250 ml. ether. The organic phase was washed twice with 100 mi. water, dried over MgSO4 and concentrated to give 5.0 g. of oil. The crude product was purified by flash chromatography with 2:3 EtOAc/hexane to give 3.7 g. of an oil (78.0 % yield).

Workup

  1. addition3 neck round bottomed flask under N2 was charged 0.9 g
  2. additionThis was followed by the addition of 3.18 g
  3. customThe reaction was quenched by the addition of 100 ml
  4. extractionwater and then extracted with 250 ml
  5. washThe organic phase was washed twice with 100 mi
  6. dry with materialwater, dried over MgSO4
  7. concentrationconcentrated
  8. customto give 5.0 g
  9. customThe crude product was purified by flash chromatography with 2:3 EtOAc/hexane
  10. customto give 3.7 g

Sources & evidence

ORD record
ord-82c1d95de66149528bcb3636f1b2cb32
Source dataset
uspto-grants-1995_03
Patent number
US05397793

Reaction notes

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