Tributylamine → Tetrabutylammonium Bromide

HRID 1658615Notes

Reaction equation

HRID 1658615 reaction equation
[CH2:1]([Br:5])[CH2:2][CH2:3][CH3:4].[CH2:6]([N:10]([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:11][CH2:12][CH2:13][CH3:14])[CH2:7][CH2:8][CH3:9]>C(#N)C>[CH3:4][CH2:3][CH2:2][CH2:1][N+:10]([CH2:11][CH2:12][CH2:13][CH3:14])([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:6][CH2:7][CH2:8][CH3:9].[Br-:5]

Participants

4

Reactant 2

HCID 7622TributylamineHCID 8002Butyl bromide

Product 1

HCID 74236Tetrabutylammonium BromideYield 87%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 60.3 g. n-butylbromide and 74.1 g. tributylamine in 100 ml chromatoquality acetonitrile was refluxed for 20 hours under argon. The reaction mixture was cooled and evaporated at 20°-30°C to near dryness. The resulting crystalline mass was washed with 300 ml cyclohexene, dissolved in 100 ml water, and further washed with cyclohexene, and then with 100 ml hexane. TBAB yield = 87 percent.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customevaporated at 20°-30°C
  3. washThe resulting crystalline mass was washed with 300 ml cyclohexene
  4. dissolutiondissolved in 100 ml water
  5. washfurther washed with cyclohexene

Sources & evidence

ORD record
ord-eba18556467c4da59da00b80c6fb2ec9
Source dataset
uspto-grants-1976_06
Patent number
US03965178

Reaction notes

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