Bromine → 2-Bromo-1-(3-chloro-4-methoxyphenyl)ethan-1-one

HRID 446818

Reaction equation

HRID 446818 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10](=[O:12])[CH3:11])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[Br:13]Br>CO>[Br:13][CH2:11][C:10]([C:4]1[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([Cl:1])[CH:3]=1)=[O:12]

Participants

4

Reactant 2

HCID 24408BromineHCID 5208573'-Chloro-4'-methoxyacetophenone

Product 1

HCID 106116132-Bromo-1-(3-chloro-4-methoxyphenyl)ethan-1-oneYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 1-(3-chloro-4-methoxyphenyl)ethanone (1.0 g, 5.42 mmol) in MeOH (29.5 mL) was added a solution of bromine (0.33 mL, 6.50 mmol) in MeOH (10 mL) at RT. The reaction mixture was then stirred for 2 h, quenched with ice and extracted with DCM (2×20 mL). The combined organic layers were washed with water, dried over Na2SO4, and concentrated in vacuo to afford 2-bromo-1-(3-chloro-4-methoxyphenyl)ethanone (1.0 g, 70%) as solid.

Workup

  1. customquenched with ice
  2. extractionextracted with DCM (2×20 mL)
  3. washThe combined organic layers were washed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-33888efdb6984ef49eddd2c1d0c0aa5e
Source dataset
uspto-grants-2013_07
Patent number
US08481534B2

Linked notes

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