Butyl bromide → HCID 12024025, compound

HRID 1730384Notes

Reaction equation

HRID 1730384 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].Br[CH2:7][CH2:8][CH2:9][CH3:10].[OH-].[Na+]>[Cl-].C(C([NH3+])(C(=O)CCCCCCC)C(=O)CCCCCCC)(=O)CCCCCCC.O>[C:3]([C:2]([C:1]#[N:5])([CH2:7][CH2:8][CH2:9][CH3:10])[CH2:7][CH2:8][CH2:9][CH3:10])#[N:4]

Participants

6

Reactant 3

HCID 8002Butyl bromideHCID 8010MalononitrileHCID 14798Sodium Hydroxide

Product 1

HCID 12024025HCID 12024025, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 77620884Tricaprylylmethyl ammonium chlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Malononitrile (128 g, 1.94 moles) was added dropwise to a mixture of 500 g (3.65 moles) of 1-bromobutane, 10 g of tricaprylylmethylammonium chloride,146 g (3.63 moles) of sodium hydroxide and 450 ml of water. The addition rate was controlled such that the temperature was maintained at 45°-50° C. After the addition was complete, the mixture was stirred for two hours longer at 50° C. The organic layer was separated and washed twice with 300 ml portions of saturated aqueous sodium chloride. The product was then distilled to give 197 g of recovered1-bromobutane and 170 g of 5,5-dicyanononane (87% selectivity based on 1-bromobutane) having a boiling point of 145° C at 30 mm Hg.

Workup

  1. temperaturewas maintained at 45°-50° C
  2. additionAfter the addition
  3. customThe organic layer was separated
  4. washwashed twice with 300 ml portions of saturated aqueous sodium chloride
  5. distillationThe product was then distilled

Sources & evidence

ORD record
ord-63af05de104847dfb10229ef444aad7a
Source dataset
uspto-grants-1976_11
Patent number
US03992432

Reaction notes

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