Tributylamine → Tetrabutylammonium Bromide

HRID 1658614Notes

Reaction equation

HRID 1658614 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 90%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 60.3 g. n-butylbromide and 74.1 g. tributylamine in 100 ml practical grade acetonitrile was refluxed for 22 hours under argon. The reaction mixture was cooled and then evaporated to near dryness at 30°C. The crystalline mass was dissolved in 100 ml water, and the aqueous solution was washed with three 100-ml aliquots of benzene. TBAB yield = 90 percent.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customevaporated
  3. customat 30°C
  4. dissolutionThe crystalline mass was dissolved in 100 ml water
  5. washthe aqueous solution was washed with three 100-ml aliquots of benzene

Sources & evidence

ORD record
ord-7ad6541de65c461391941f1f71995a40
Source dataset
uspto-grants-1976_06
Patent number
US03965178

Reaction notes

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