Phenylacetaldehyde → 2-Bromo-2-phenylacetaldehyde

HRID 2409898Notes

Reaction equation

HRID 2409898 reaction equation
[C:1]1([CH2:7][CH:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:10]Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:10][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH:8]=[O:9]

Participants

5

Reactant 3

HCID 998PhenylacetaldehydeHCID 24408BromineHCID 516892Sodium Bicarbonate

Product 1

HCID 108889012-Bromo-2-phenylacetaldehydeYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of phenyl-acetaldehyde (1 g, 8.3 mmol) in CH2Cl2 (3 mL) was added dropwise a solution of Br2 (1.3 g, 8.3 mmol) in CH2Cl2 (3 mL) at −10° C. over 30 min. The resulting solution was allowed to warm to rt and then heated to reflux overnight. Aqueous NaHCO3 was added to the cooled mixture and the solution was extracted with CH2Cl2. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated to afford crude bromo-phenyl-acetaldehyde (1 g, 5.05 mmol, 61%) as a green liquid which was taken to the next step directly. Anal. Calcd. for C8H7BrO m/z 198.0, found: 198.0 GC-MS (M)+.

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. extractionthe solution was extracted with CH2Cl2
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d0e2d0f41d1a40a7bb620d984b3c7d59
Source dataset
uspto-grants-2014_08
Patent number
US08815909B2

Reaction notes

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