2-Bromopropane → HCID 21181206, compound

HRID 1386522Notes

Reaction equation

HRID 1386522 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 75.5%

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Procedure

A mixture of 2,6-difluorophenylacetonitrile (10.0 g, 65.4 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: 11H 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-4ec4e3565b534dbfab10b5accaed4475
Source dataset
uspto-grants-2001_07
Patent number
US06265439B1

Reaction notes

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