Hydrogen Bromide → 1-(1-Bromoethyl)-3-nitrobenzene

HRID 1970861Notes

Reaction equation

HRID 1970861 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10](O)[CH3:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[BrH:13]>C(O)(=O)C.C(Cl)Cl>[Br:13][CH:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[CH3:11]

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 223135alpha-Methyl-3-nitrobenzenemethanol

Product 1

HCID 229178381-(1-Bromoethyl)-3-nitrobenzene

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 6344DichloromethaneSolvent

Procedure

26.15 g (156 mmol) of 1-(3-nitrophenyl)ethanol are dissolved in 130 ml of glacial acetic acid, and 55 ml (313 mmol) of 33% HBr in glacial acetic acid are added dropwise with ice cooling. The reaction mixture is stirred at room temperature for 5 days. The mixture is subsequently diluted with 300 ml of DCM, washed with 3×200 ml of H2O and 200 ml of saturated NaHCO3 solution, dried over sodium sulfate and evaporated to dryness, and the residue is crystallised from petroleum ether.

Workup

  1. washwashed with 3×200 ml of H2O and 200 ml of saturated NaHCO3 solution
  2. dry with materialdried over sodium sulfate
  3. customevaporated to dryness
  4. customthe residue is crystallised from petroleum ether

Sources & evidence

ORD record
ord-26e5f94bbbb64bf9adb31032db0c486d
Source dataset
uspto-grants-2013_04
Patent number
US08431572B2

Reaction notes

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