Water → 2-(4-Fluoronaphthalen-1-yl)acetonitrile

HRID 8212Notes

Reaction equation

HRID 8212 reaction equation
Cl[CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([F:13])=[CH:5][CH:4]=1.[C-:14]#[N:15].[Na+].O>CN(C)C=O>[F:13][C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]([CH2:2][C:14]#[N:15])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 156574171-(Chloromethyl)-4-fluoronaphthalene

Product 1

HCID 219925322-(4-Fluoronaphthalen-1-yl)acetonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 1-chloromethyl-4-fluoronaphthalene (5.45 g, 5.66 mmol), sodium cyanide (333 mg, 6.79 mmol), and water (2 mL) in N,N-dimethylformamide (30 mL) is stirred for 8 h, then heated at 70° C. for 15 h. The mixture is cooled to room temperature and partitioned between saturated sodium bicarbonate solution and ethyl acetate. The organic portion is washed with three portions of water, one portion of brine, dried (sodium sulfate), filtered and evaporated. The residue is chromatographed on SiO2 (30% ethyl acetate/hexane) to yield the title compound, 4.67 g (90%), as a light brown solid. 1H NMR (CDCl3): δ 8.19 (d, J=8 Hz, 1H), 7.87 (d, J=8 Hz, 1H), 7.68 (ddd, J=8, 7, 1 Hz, 1H), 7.63 (ddd, J=8, 7, 1 Hz, 1H), 7.51 (dd, J=8, 5 Hz, 1H), 7.14 (dd, J=10, 8 Hz, 1H), 4.09 (s, 2H).

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. custompartitioned between saturated sodium bicarbonate solution and ethyl acetate
  3. washThe organic portion is washed with three portions of water, one portion of brine
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is chromatographed on SiO2 (30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-fd8e422ad9204a379e007b50fb4602f2
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Reaction notes

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