Dimethylformamide → 2-(4-Bromo-2-fluorophenyl)-2-methylpropanenitrile

HRID 1453068Notes

Reaction equation

HRID 1453068 reaction equation
[CH3:1]I.[H-].[Na+].[Br:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]#N)=[C:8]([F:15])[CH:7]=1.C[N:17]([CH:19]=O)C>>[Br:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([CH3:1])([CH3:13])[C:19]#[N:17])=[C:8]([F:15])[CH:7]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 71723082-(4-Bromo-2-fluorophenyl)acetonitrile

Product 1

HCID 534036182-(4-Bromo-2-fluorophenyl)-2-methylpropanenitrileYield 77%

Procedure

To a solution of MeI (3.2 mL, 49.3 mmol) in anhydrous DMF (82 mL) at 0° C. was added NaH (60%, 2.0 g), followed by (4-bromo-2-fluorophenyl)acetonitrile (3.5 g, 16.4 mmol). The mixture was slowly warmed up to room temperature and stirred for 3 hours. The reaction was quenched by the addition of saturated NH4Cl and extracted with EtOAc (3×150 mL). The combined organic extracts were washed with brine, dried with Na2SO4 and evaporated to dryness. The mixture was purified by flash column chromatography (0-20% EtOAc in hexanes) to give the product (3.0 g, 77% yield). 1H NMR (300 MHz, CDCl3) δ: 1.78 (s, 6H), 7.26-7.42 (m, 3H).

Workup

  1. customThe reaction was quenched by the addition of saturated NH4Cl
  2. extractionextracted with EtOAc (3×150 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried with Na2SO4
  5. customevaporated to dryness
  6. customThe mixture was purified by flash column chromatography (0-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-aa018793ffd442ca9c0d08b25d52a114
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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