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

HRID 539786

Reaction equation

HRID 539786 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[Br:14]Br>C(Cl)Cl>[Br:14][CH2:9][C:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=1)=[O:10]

Participants

4

Reactant 2

HCID 24408BromineHCID 792463'-Nitro-4'-methylacetophenone

Product 1

HCID 38004222-Bromo-1-(4-methyl-3-nitrophenyl)ethan-1-oneYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(4-methyl-3-nitro-phenyl)ethanone (Sigma-Aldrich, 25.08 g, 0.14 mol) in CH2Cl2 (269 mL) is cooled to 0° C. To this is added bromine (7.17 mL, 0.14 mol) at 0° C. with stirring. The reaction mixture is allowed to warm slowly to rt over a total of 90 minutes. Ice water (500 mL) is added, organics are collected and aqueous layer is extracted with CH2Cl2 (2×250 mL). The organic layers are combined, washed with water, dried with Na2SO4 and concentrated to give the title compound (36.1 g, 99% yield). LCMS m/z=258.3, 260.2 [M+H]+, tR=2.39 min.

Workup

  1. customorganics are collected
  2. extractionaqueous layer is extracted with CH2Cl2 (2×250 mL)
  3. washwashed with water
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c3f1d1931a8242a583beeaf89dc254d6
Source dataset
uspto-grants-2014_10
Patent number
US08871767B2

Linked notes

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