Bromine → Ethyl 4-(2-bromoacetyl)benzoate

HRID 650994

Reaction equation

HRID 650994 reaction equation
[C:1]([C:4]1[CH:14]=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[Br:15]Br.C([O-])(O)=O.[Na+]>CCOCC.[Cl-].[Al+3].[Cl-].[Cl-]>[Br:15][CH2:2][C:1]([C:4]1[CH:14]=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][CH:5]=1)=[O:3]

Participants

6

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 600911Ethyl 4-acetylbenzoate

Product 1

HCID 11966043Ethyl 4-(2-bromoacetyl)benzoateYield 81.7%

Reagents, catalysts & solvents 2

HCID 6451240Aluminum(III) ChlorideCatalystHCID 3283Diethyl EtherSolvent

Procedure

To a solution of ethyl 4-acetylbenzoate (5.12 g, 26.6 mmol) in ether (50 ml) containing aluminium chloride (0.025 g, 0.19 mmol) is added bromine (1.31 ml, 26.6 mmol) and the reaction mixture is stirred for 2 h. The reaction mixture is poured into saturated NaHCO3 solution and stirred for 30 min. and the layers are separated. The organic layer is washed with NaHCO3, H2O, dried over MgSO4, concentrated to half of its volume and refrigerated overnight. The resulting solid is filtered to yield ethyl 4-(2′-bromoacetyl)benzoate (5.89 g, 81.6%) as white crystals.

Workup

  1. stirringstirred for 30 min.
  2. customthe layers are separated
  3. washThe organic layer is washed with NaHCO3, H2O
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated to half of its volume and refrigerated overnight
  6. filtrationThe resulting solid is filtered

Sources & evidence

ORD record
ord-e7d54fee998740bcb97886bfbd404b82
Source dataset
uspto-grants-2001_08
Patent number
US06277873B1

Linked notes

Loading…