2-Bromopropane → HCID 14245132, compound

HRID 2399828Notes

Reaction equation

HRID 2399828 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]#[N:10].[OH-].[Na+].Br[CH:14]([CH3:16])[CH3:15]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH:14]([CH3:16])[CH3:15])[C:9]#[N:10]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 14798Sodium Hydroxide2×HCID 67592Benzeneacetonitrile, 2-fluoro-

Product 1

HCID 14245132HCID 14245132, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 70681Tetrabutylammonium ChlorideCatalyst

Procedure

A mixture of 2-fluorophenylacetonitrile (10.0 g, 74.1 mmoles), 50% aqueous sodium hydroxide (5.2 g), sodium hydroxide (741 mg), tetra-n-butylammonium chloride (3.3 g), and 2-bromopropane (10.0 g, 81.5 mmoles) was stirred rapidly while heating from room temperature to 60°-65°. The temperature was increased to 90°-95 and so maintained for 1.0 hour. After cooling, the mixture was partitioned between diethyl ether and water. The organic layer was washed with brine, dried over sodium sulfate, filtered, and the solvent evaporated. Chromatography of the residue over silica gel using 30% methylene chloride-hexane as eluent gave a compound (9.35 g) as a water-white oil which was characterized by NMR, as follows: 1H NMR(CDCl3) d 7.51-7.00 (m, 4H), 3.99 (d, 1H), 2.22 (m, 1H), 1.06 (d, 1H).

Workup

  1. temperatureThe temperature was increased to 90°-95
  2. temperatureso maintained for 1.0 hour
  3. temperatureAfter cooling
  4. customthe mixture was partitioned between diethyl ether and water
  5. washThe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent evaporated

Sources & evidence

ORD record
ord-f7641f6320114c448533504b07d8abbb
Source dataset
uspto-grants-1995_09
Patent number
US05451604

Reaction notes

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