Diethyl Ether → 2-Bromo-1-(3-methylphenyl)ethan-1-one

HRID 450025

Reaction equation

HRID 450025 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][CH:4]=[C:3]([C:7](=[O:9])[CH3:8])[CH:2]=1.[Br:11]Br.CCOCC>O1CCOCC1>[Br:11][CH2:8][C:7]([C:3]1[CH:2]=[C:1]([CH3:10])[CH:6]=[CH:5][CH:4]=1)=[O:9]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 114553-MethylacetophenoneHCID 24408Bromine

Product 1

HCID 100361292-Bromo-1-(3-methylphenyl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 1-m-tolyl-ethanone (6.0 g, 44.72 mmol) in dioxane (5 ml), bromine (7.14 g, 44.72 mmol) in dioxane (10 ml) and ether (15 ml) was added and stirred at room temperature for 5 hr. The reaction mixture was poured into ice water and the compound was extracted using ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, filtered and then evaporated to give crude 2-bromo-1-m-tolyl-ethanone, 7.6 g (80%). The crude compound obtained was used in the next step without further purification.

Workup

  1. extractionthe compound was extracted
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customto give crude 2-bromo-1-m-tolyl-ethanone, 7.6 g (80%)

Sources & evidence

ORD record
ord-0586c48dda1c4b35beae4608fb38fbc0
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Linked notes

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