Diethyl Ether → 1-(4-Bromophenyl)-2-methylpropan-1-one

HRID 361464Notes

Reaction equation

HRID 361464 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#N)=[CH:4][CH:3]=1.[CH:10]([Mg]Cl)([CH3:12])[CH3:11].[Cl-].[NH4+].C([O:19]CC)C>>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6](=[O:19])[CH:10]([CH3:12])[CH3:11])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 3283Diethyl Ether2×HCID 12162Benzonitrile, 4-bromo-HCID 25517Ammonium ChlorideHCID 178418918HCID 178418918, compound

Product 1

HCID 150747831-(4-Bromophenyl)-2-methylpropan-1-one

Procedure

4-Bromobenzonitrile (10 g) was dissolved in anhydrous diethyl ether (125 ml) and 2M isopropyl magnesium chloride in diethyl ether (30.24 ml) was added dropwise with stirring. The resulting solution was then heated to reflux for 18 hours. The reaction mixture was allowed to cool to ambient temperature and a saturated aqueous solution of ammonium chloride was added slowly with stirring. Stirring was continued for a further 2 hours. The organic phase was separated and the aqueous layer was extracted with diethyl ether (3×100 ml). The combined organic phases were washed with water (50 ml), then brine (50 ml), dried (MgSO4) and evaporated to give 1-bromo-4-(2-methylpropanoyl)benzene (11.6 g); 1H NMR (CDCl3): 1.15 (d, 6 H), 3.1 (septet, 1 H), 7.5-7.6 (m, 4 H); mass spectrum (CI+) 226 (M.)+.

Workup

  1. temperatureThe resulting solution was then heated
  2. temperatureto reflux for 18 hours
  3. stirringwith stirring
  4. stirringStirring
  5. customThe organic phase was separated
  6. extractionthe aqueous layer was extracted with diethyl ether (3×100 ml)
  7. washThe combined organic phases were washed with water (50 ml)
  8. dry with materialbrine (50 ml), dried (MgSO4)
  9. customevaporated

Sources & evidence

ORD record
ord-dfbe257ee01d46c68f96fc215277225c
Source dataset
uspto-grants-1999_02
Patent number
US05866568

Reaction notes

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