N,N-Diethylaniline → Benzenamine, 4-bromo-N,N-diethyl-

HRID 2249160Notes

Reaction equation

HRID 2249160 reaction equation
[Br:1]Br.[CH2:3]([N:5]([CH2:12][CH3:13])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH3:4]>C(O)(=O)C>[CH2:12]([N:5]([C:6]1[CH:11]=[CH:10][C:9]([Br:1])=[CH:8][CH:7]=1)[CH2:3][CH3:4])[CH3:13]

Participants

4

Reactant 2

HCID 7061N,N-DiethylanilineHCID 24408Bromine

Product 1

HCID 16328Benzenamine, 4-bromo-N,N-diethyl-Yield 95.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

93 g of bromine were added dropwise to a solution of 86 g of N,N-diethylaniline in 400 ml of acetic acid and the mixture was poured into an ice-water mixture. The mixture was extracted with methylene chloride and the organic phase was washed with aqueous sodium bicarbonate solution, dried and evaporated to dryness to obtain 125 g of 4-(N,N-diethylamino)-bromobenzene boiling at 97° C. at 0.6 mm Hg.

Workup

  1. extractionThe mixture was extracted with methylene chloride
  2. washthe organic phase was washed with aqueous sodium bicarbonate solution
  3. customdried
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-9d2b0f2099fd44199a10fee6231f6d74
Source dataset
uspto-grants-1991_08
Patent number
US05043332

Reaction notes

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