2-Bromopropane → HCID 21181229, compound

HRID 1386515Notes

Reaction equation

HRID 1386515 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]#[N:11])=[CH:5][CH:4]=1.[OH-].[Na+].Br[CH:17]([CH3:19])[CH3:18]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:1][C:2]([F:12])([F:13])[C:3]1[CH:4]=[CH:5][C:6]([CH:9]([CH:17]([CH3:19])[CH3:18])[C:10]#[N:11])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 14798Sodium Hydroxide2×HCID 753594-(Trifluoromethyl)phenylacetonitrile

Product 1

HCID 21181229HCID 21181229, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 70681Tetrabutylammonium ChlorideCatalyst

Procedure

To a mixture of 4-trifluoromethyl-phenylacetonitrile (5.00 g, 27.0 mmoles), 50% aqueous sodium hydroxide solution (1.9 g), sodium hydroxide (270 mg), and tetra n-butylammonium chloride (1.2 g) stirring in a 60° oil bath was added 2-bromopropane (3.32 g, 27.0 mmoles). The resulting mixture was stirred at 80° for 0.5 hours, and then at 90-95° for 1.0 hours longer. After cooling, the mixture was partitioned between toluene and water. The organic layer was washed with water, dried over anhydrous sodium sulfate, filtered and then evaporated. Chromatography of the residue over silica gel using 10% ethyl acetate-hexane as eluent gave the title compound (3.95 g) as an orange oil which was characterized by NMR as follows: 1H NMR (CDCl3) d 7.67(d, 2H), 7.48(d, 2H), 3.77(d, 1H), 2.18(m, 1H), 1.13(d, 3H), 1.06(d, 3H).

Workup

  1. stirringThe resulting mixture was stirred at 80° for 0.5 hours
  2. temperatureAfter cooling
  3. customthe mixture was partitioned between toluene and water
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-9fcf1b51cbe049f19412326fbcd558b1
Source dataset
uspto-grants-2001_07
Patent number
US06265439B1

Reaction notes

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