Tetrahydrofuran → 4'-Benzyloxy-2-bromopropiophenone

HRID 2217783Notes

Reaction equation

HRID 2217783 reaction equation
O1CCCC1.[CH3:6][CH2:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:12][CH:11]=1)=[O:9].[Br:24]Br.C(=O)([O-])O.[Na+]>CCCCCC.C(OCC)(=O)C>[CH2:17]([O:16][C:13]1[CH:14]=[CH:15][C:10]([C:8](=[O:9])[CH:7]([Br:24])[CH3:6])=[CH:11][CH:12]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 24408BromineHCID 78246p-BenzyloxypropiophenoneHCID 516892Sodium Bicarbonate

Product 1

HCID 1000404'-Benzyloxy-2-bromopropiophenoneYield 97.5%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To 100 mL of a tetrahydrofuran solution of 24.00 g (100 mmol) of 4-benzyloxypropiophenone, a hexane solution (20 mL) of 23.973 g (1.5 equivalents) of bromine was gradually added at 20° C., followed by 1 hour of stirring. To the resulting solution, 50 mL of a saturated sodium hydrogen carbonate solution and 100 mL of ethyl acetate were added to conduct extraction. The organic layer was washed with 30 mL of a 20 wt % sodium thiosulfate aqueous solution, dried over anhydrous magnesium sulfate, and subjected to distillation under a reduced pressure to remove the solvents. A colorless, oily substance was obtained as a result. To this substance, 200 mL of hexane was added to precipitate crystals. White crystals (31.12 g; isolation yield: 95%) of 1-[4-(benzyloxy)phenyl]-2-bromo-1-propanone were obtained as a result.

Workup

  1. extractionextraction
  2. washThe organic layer was washed with 30 mL of a 20 wt % sodium thiosulfate aqueous solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationsubjected to distillation under a reduced pressure
  5. customto remove the solvents
  6. customA colorless, oily substance was obtained as a result
  7. customto precipitate crystals

Sources & evidence

ORD record
ord-4402d61fa5964742a25301c169c815a9
Source dataset
uspto-grants-2008_08
Patent number
US07408084B2

Reaction notes

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