2,6-Diethylaniline → 4-Bromo-2,6-diethylaniline

HRID 1955142Notes

Reaction equation

HRID 1955142 reaction equation
[CH2:1]([C:3]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH3:11])[C:4]=1[NH2:5])[CH3:2].[Br:12]Br>C(O)(=O)C.C(OCC)C>[Br:12][C:8]1[CH:7]=[C:6]([CH2:10][CH3:11])[C:4]([NH2:5])=[C:3]([CH2:1][CH3:2])[CH:9]=1

Participants

5

Reactant 2

HCID 113692,6-DiethylanilineHCID 24408Bromine

Product 1

HCID 6114524-Bromo-2,6-diethylanilineYield 21.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 2,6-diethylaniline (10.0 g, 67.0 mmol) in acetic acid (50 mL) at ambient temperature was added bromine (10.4 mL, 201 mmol). The reaction was stirred overnight at ambient temperature. The reaction mixture was diluted with diethyl ether (200 mL) and washed with 5% sodium bisulfite (4×50 mL) and brine. The organic phase was dried with sodium sulfate and the solvents were removed in vacuo. The residue was chromatographed on silica gel, eluting with 9:1 hexane-ethyl acetate to give the title compound (3.28 g, 21 % yield).

Workup

  1. washwashed with 5% sodium bisulfite (4×50 mL) and brine
  2. dry with materialThe organic phase was dried with sodium sulfate
  3. customthe solvents were removed in vacuo
  4. customThe residue was chromatographed on silica gel
  5. washeluting with 9:1 hexane-ethyl acetate

Sources & evidence

ORD record
ord-d129ebdc38ad42a88d1ac8f8384a56c2
Source dataset
uspto-grants-2000_09
Patent number
US06124341

Reaction notes

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