2-Bromopropane → HCID 21181206, compound

HRID 2399829Notes

Reaction equation

HRID 2399829 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH2:9][C:10]#[N:11].[OH-].[Na+].Br[CH:15]([CH3:17])[CH3:16]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH:9]([CH:15]([CH3:17])[CH3:16])[C:10]#[N:11]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 14798Sodium Hydroxide2×HCID 69559(2,6-Difluorophenyl)acetonitrile

Product 1

HCID 21181206HCID 21181206, compoundYield 914.5%

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Procedure

A mixture of 2,6-difluorophenylacetonitrile (10.0 g, 5.4 mmoles), 50% aqueous sodium hydroxide (4.6 g), sodium hydroxide (653 mg), tetra-n-butylammonium bromide (2.90 g and 2-bromopropane (8.85 g, 71.9 mmoles) was stirred while heating to 80°-85° over 1.0 hours, and then maintained at that temperature for 2.0 hours. After cooling, the mixture was partitioned between diethyl ether and water, the aqueous layer extracted with ether and the combined organic extracts washed with brine, dried over magnesium sulfate, filtered and the solvent evaporated. The residue was distilled to give a product compound (9.64 g) as a water-white liquid, b.p. 92°-94° (3 mm) which was characterized by NMR as follows: 1 1H NMR (CDCl)3 d 7.32 (m, 1H), 6.95 (m, 2H), 3.84 (d, 1H), 2.32 (m, 1H), 1.24 (d, 3H), 0.89 (d, 3H).

Workup

  1. temperaturewhile heating to 80°-85° over 1.0 hours
  2. temperaturemaintained at that temperature for 2.0 hours
  3. temperatureAfter cooling
  4. customthe mixture was partitioned between diethyl ether and water
  5. extractionthe aqueous layer extracted with ether
  6. washthe combined organic extracts washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent evaporated
  10. distillationThe residue was distilled

Sources & evidence

ORD record
ord-464217d3c88f4ab3ae16359a3ef9dd91
Source dataset
uspto-grants-1995_09
Patent number
US05451604

Reaction notes

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