Bromine → 2-Bromo-1-(2,5-dichlorophenyl)ethanone

HRID 626924Notes

Reaction equation

HRID 626924 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[Cl:11])=[O:3].[Br:12]Br.C([O-])(O)=O.[Na+]>C(OCC)C>[Br:12][CH2:1][C:2]([C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[Cl:11])=[O:3]

Participants

5

Reactant 3

HCID 24408BromineHCID 75587Ethanone, 1-(2,5-dichlorophenyl)-HCID 516892Sodium Bicarbonate

Product 1

HCID 27569072-Bromo-1-(2,5-dichlorophenyl)ethanoneYield 68%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

2,5-Dichloroacetophenone (20.9 g, 0.11 mol) was dissolved in diethyl ether (300 mL) and the reaction mixture was cooled to 0° C. Bromine (5.66 mL, 0.11 mol) was added slowly dropwise and the reaction mixture was allowed to warm to room temperature over 20 minutes. The reaction mixture was treated with saturated aqueous NaHCO3 solution (250 mL). The organic layer was separated, dried over MgSO4 and concentrated in vacuo, yielding the title compound (20.0 g, 68%) as a yellow oil. δH (d6-DMSO) 7.94 (dd, J 2.2, 0.3 Hz, 1H), 7.61 (m, 2H), 4.88 (s, 2H).

Workup

  1. temperatureto warm to room temperature over 20 minutes
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-46ac63a7b79e4dbc9ebfea0ee9738e56
Source dataset
uspto-grants-2016_04
Patent number
US09309243B2

Reaction notes

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