1-Acetylnaphthalene → 2-Bromo-1-(1-naphthalenyl)ethanone

HRID 386394

Reaction equation

HRID 386394 reaction equation
[C:1]1([C:11](=[O:13])[CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Br:14]Br>O1CCOCC1>[Br:14][CH2:12][C:11]([C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)=[O:13]

Participants

4

Reactant 2

HCID 136631-AcetylnaphthaleneHCID 24408Bromine

Product 1

HCID 38305132-Bromo-1-(1-naphthalenyl)ethanoneYield 93.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 1-(naphthalen-1-yl)ethanone (500 mg, 2.9 mmol) in dioxane (5 mL) was added to a solution of bromine (510 mg, 3.19 mmol) in dioxane (10 mL), at room temperature, over a period of 30 minutes. The reaction mixture was then stirred at room temperature for 20 minutes and concentrated. The resulting residue was diluted with ether and washed with saturated sodium bicarbonate, water, dried over sodium sulfate and concentrated. Purification by preparative thin layer chromatography (70% DCM/30% hexanes) afforded 2-bromo-1-(naphthalen-1-yl)ethanone (673 mg, 93%).

Workup

  1. concentrationconcentrated
  2. additionThe resulting residue was diluted with ether
  3. washwashed with saturated sodium bicarbonate, water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customPurification by preparative thin layer chromatography (70% DCM/30% hexanes)

Sources & evidence

ORD record
ord-28433479610f4dd89803e5dd0db30856
Source dataset
uspto-grants-2013_02
Patent number
US08372807B2

Linked notes

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