HCID 17986946, compound → 4-(4-Fluorophenyl)butanenitrile

HRID 2374731Notes

Reaction equation

HRID 2374731 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([NH2:13])=O)=[CH:4][CH:3]=1>FC(F)(F)C(OC(=O)C(F)(F)F)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][C:11]#[N:13])=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 17986946HCID 17986946, compound

Product 1

HCID 198754764-(4-Fluorophenyl)butanenitrileYield 100%

Reagents, catalysts & solvents 1

HCID 9845Trifluoroacetic anhydrideSolvent

Procedure

4-(4-Fluorophenyl)-butyramide (Int. A4) (2.63 g) was dissolved in trifluoroacetic anhydride (10 ml) and stirred for 2 h. The solution was concentrated and then dissolved in dichloromethane and washed with 2N sodium hydroxide solution. The organics extracts were isolated, dried (MgSO4) and concentrated to yield the product (2.3 g, 100%) which contained ˜5% starting amide as an impurity. 1H-NMR (CDCl3) δ 1.96 (2H, app q), 2.31 (2H, t), 2.75 (2H, t), 6.98 (2H, m), 7.14 (2H, m). MS (APCI+) M+1=164, C10H10FN requires 163.

Workup

  1. concentrationThe solution was concentrated
  2. dissolutiondissolved in dichloromethane
  3. washwashed with 2N sodium hydroxide solution
  4. customThe organics extracts were isolated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-abf5bc582fd84fdbaa8c948644bb80ef
Source dataset
uspto-grants-2008_12
Patent number
US07462620B2

Reaction notes

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