Tributylamine → 4-(Bromomethyl)benzyltri-n-butylammonium bromide

HRID 2399650

Reaction equation

HRID 2399650 reaction equation
[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][Br:10])=[CH:5][CH:4]=1.[CH2:11]([N:15]([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH2:18][CH3:19])[CH2:12][CH2:13][CH3:14].C([NH+](CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[Br-:1].[Br:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][N+:15]([CH2:16][CH2:17][CH2:18][CH3:19])([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:11][CH2:12][CH2:13][CH3:14])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 7622TributylamineHCID 693351,4-Bis(bromomethyl)benzeneHCID 3724478Tributylammonium

Product 1

HCID 190321784-(Bromomethyl)benzyltri-n-butylammonium bromide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of α,α'-dibromo-p-xylene (7.0 g, 26.5 mmol) in toluene (200 mL) was added tri-n-butylamine (3.43 g, 18.6 mmol) under argon gas. The reaction mixture was stirred for several days at room temperature under argon at which time the tri-n-butylammonium salt had crystallized out of solution. The crystals were filtered and washed with toluene (3×50 mL) and hexanes (3×50 mL) and dried: 1H NMR (CDCl3) δ 0.97 (t, 9H), 1.39 (m, 6H), 1.76 (m, 6H), 3.32 (m, 6H), 4.47 (s, 2H), 4.96 (s, 2H), 7.42-7.59 (dd, 4H).

Workup

  1. customhad crystallized out of solution
  2. filtrationThe crystals were filtered
  3. washwashed with toluene (3×50 mL) and hexanes (3×50 mL)
  4. customdried

Sources & evidence

ORD record
ord-8eace780a4074ab4a5de6617303541df
Source dataset
uspto-grants-1995_09
Patent number
US05451347

Linked notes

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