Bromine → 2-Bromo-1'-propionaphthone

HRID 1928573Notes

Reaction equation

HRID 1928573 reaction equation
[Br:1]Br.[CH3:3][CH2:4][C:5]([C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1)=[O:6]>C(O)C>[Br:1][CH:4]([CH3:3])[C:5]([C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1)=[O:6]

Participants

4

Reactant 2

HCID 24408BromineHCID 2311591-Naphthalen-1-ylpropan-1-one

Product 1

HCID 2311612-Bromo-1'-propionaphthone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

53.3 g (0.334 mol) of bromine was added dropwise to a solution consisting of 61.1 g (0.332 mol) of 1-propionaphthone and 180 mL of ethanol at 50 to 55° C. After completion of addition, the ethanol was distilled off in vacuo, and the resulting concentrate was dissolved in 130 mL of toluene, washed with a mixed aqueous solution of sodium bicarbonate and sodium chloride (150 mL×two times), and then dried over sodium sulfate to obtain a toluene solution of 2-bromo-1′-propionaphthone.

Workup

  1. additionAfter completion of addition
  2. distillationthe ethanol was distilled off in vacuo
  3. concentrationthe resulting concentrate
  4. dissolutionwas dissolved in 130 mL of toluene
  5. washwashed with a mixed aqueous solution of sodium bicarbonate and sodium chloride (150 mL×two times)
  6. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-3dc97c6b44f246fabbad5bf473138d78
Source dataset
uspto-grants-2012_05
Patent number
US08183386B2

Reaction notes

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