Bromine → 2-Bromo-1-(4-methyl-3-nitrophenyl)propan-1-one

HRID 539771

Reaction equation

HRID 539771 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:11])[CH2:9][CH3:10])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[Br:15]Br>C(Cl)Cl>[Br:15][CH:9]([CH3:10])[C:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([N+:12]([O-:14])=[O:13])[CH:4]=1)=[O:11]

Participants

4

Reactant 2

HCID 24408BromineHCID 232442491-(4-Methyl-3-nitrophenyl)propan-1-one

Product 1

HCID 575162742-Bromo-1-(4-methyl-3-nitrophenyl)propan-1-oneYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-methyl-3-nitrophenyl)propan-1-one (6.6 g, 34.1 mmol) in CH2Cl2 (200 mL) is added bromine (34.1 mmol) dropwise over 20 minutes. The reaction is stirred for 4 hours at room temp. and then washed with sat. aqueous NaHCO3 (100 mL), organic layer is collected, dried over Na2SO4, filtered and concentrated to dryness to afford 9.0 g (97%) of the title compound as an orange oil: Rf 0.53 (1:1 CH2Cl2:hexanes).

Workup

  1. washwashed with sat. aqueous NaHCO3 (100 mL), organic layer
  2. customis collected
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-6f40bf183d504c9aac2e7f904bd40d43
Source dataset
uspto-grants-2014_10
Patent number
US08871767B2

Linked notes

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