Water → 1-Bromo-9-phenylnonan-2-one

HRID 1420528Notes

Reaction equation

HRID 1420528 reaction equation
[Br:1]Br.[C:3]1([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16](=[O:18])[CH3:17])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.O>CO.CCOCC>[Br:1][CH2:17][C:16](=[O:18])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 962Water2×HCID 24408BromineHCID 187819999-Phenylnonan-2-one

Product 1

HCID 187820321-Bromo-9-phenylnonan-2-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

Bromine (5.21 g, 0.033 mol) was added to a solution of 9-phenylnonan-2-one (7.12 g, 0.033 mol) in dry methanol (75 ml) and stirred for 2 hours at room temperature. Water (50 ml) was added and stirring continued for 18 hours at room temperature. Ether (175 ml) and water (100 ml) were added, the organic layer washed with dil. NaHCO3, water (×2), dried (MgSO4) and evaporated under reduced pressure to an oil (5.39 g). Petroleum ether (40° C.-60° C., 50 ml) was added and the mixture cooled to -10° C. and filtered. The solid obtained was re-dissolved in ether (40 ml) and evaporated under reduced pressure to an oil (4.06 g) which was was further purified by flash chromatography on silica gel using hexane/ethyl acetate to give 1-bromo-9-phenylnonan-2-one a pale yellow solid (3.80 g, 39%).

Workup

  1. stirringstirring
  2. waitcontinued for 18 hours at room temperature
  3. washthe organic layer washed with dil. NaHCO3, water (×2)
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure to an oil (5.39 g)
  6. additionPetroleum ether (40° C.-60° C., 50 ml) was added
  7. temperaturethe mixture cooled to -10° C.
  8. filtrationfiltered
  9. customThe solid obtained
  10. customevaporated under reduced pressure to an oil (4.06 g) which
  11. customwas was further purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-bf89828e1b2b43259dc025e0fe4c08b8
Source dataset
uspto-grants-2000_06
Patent number
US06071899

Reaction notes

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