1-Bromo-4-ethylbenzene → HCID 67459476, compound

HRID 554570Notes

Reaction equation

HRID 554570 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH3:10])=[CH:5][CH:4]=1.[Br:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[O:20][CH2:21][CH3:22])[CH:15]=[O:16].[Cl-].[NH4+]>C1COCC1>[Br:11][C:12]1[CH:13]=[C:14]([CH:15]([C:3]2[CH:8]=[CH:7][C:6]([CH2:9][CH3:10])=[CH:5][CH:4]=2)[OH:16])[CH:17]=[CH:18][C:19]=1[O:20][CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 153131-Bromo-4-ethylbenzeneHCID 25517Ammonium ChlorideHCID 14943363-bromo-4-ethoxybenzaldehydeHCID 5462224Magnesium

Product 1

HCID 67459476HCID 67459476, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

THF (10 mL) was added to magnesium (353 mg, 14.5 mmol), and furthermore 1-bromo-4-ethylbenzene (2 mL, 14.5 mmol) was added dropwise thereto and the mixture was heated to reflux for one hour. The reaction mixture was cooled to 0° C., and a solution of 3-bromo-4-ethoxybenzaldehyde (2.21 g, 9.68 mmol) in THF (5 mL) was added thereto and the reaction mixture was stirred at the same temperature for 1.5 hours. To the reaction mixture, a saturated ammonium chloride aqueous solution was added and the resulting mixture was extracted with ethyl acetate. The extract was washed with a saturated sodium chloride aqueous solution and dried over magnesium sulfate. The residue obtained by distilling the solvent under reduced pressure was purified by silica gel column chromatography [developing solution=n-hexane to n-hexane:ethyl acetate (3:1)] to obtain the title compound (2.83 g, 88%).

Workup

  1. additionwas added dropwise
  2. temperaturethe mixture was heated
  3. temperatureto reflux for one hour
  4. extractionthe resulting mixture was extracted with ethyl acetate
  5. washThe extract was washed with a saturated sodium chloride aqueous solution
  6. dry with materialdried over magnesium sulfate
  7. customThe residue obtained
  8. distillationby distilling the solvent under reduced pressure
  9. customwas purified by silica gel column chromatography [developing solution=n-hexane to n-hexane:ethyl acetate (3:1)]

Sources & evidence

ORD record
ord-3e789edc0c9e4239b75b4119009ea7ee
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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