4'-Hydroxypropiophenone → HCID 23070398, compound

HRID 2217786Notes

Reaction equation

HRID 2217786 reaction equation
O1CCCC1.[OH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:16])[CH2:14][CH3:15])=[CH:9][CH:8]=1.C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>C(OCC)(=O)C.O>[CH3:24][S:25]([O:6][C:7]1[CH:8]=[CH:9][C:10]([C:13](=[O:16])[CH2:14][CH3:15])=[CH:11][CH:12]=1)(=[O:27])=[O:26]

Participants

7

Reactant 4

HCID 62714'-HydroxypropiophenoneHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 23070398HCID 23070398, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A tetrahydrofuran solution (50 mL) of 15.0 g (100 mmol) of p-hydroxypropiophenone and 12.143 g (1.2 equivalents) of triethylamine was cooled to 5° C. To this solution, 12.60 g (1.1 equivalents) of methanesulfonyl chloride was added dropwise over 30 minutes, followed by 1 hour of stirring. To the resulting solution, 40 mL of water and 70 mL of ethyl acetate were added to conduct extraction. The organic layer was washed with 50 mL of saturated brine, dried over anhydrous magnesium sulfate, and subjected to distillation under a reduced pressure to remove the solvents. A white solid was obtained as a result. This white solid was crystallized from 40 mL of ethyl acetate and 120 mL of hexane to thereby obtain white crystals of p-(methanesulfonyloxy)propiophenone (21.17 g, isolation yield: 93%). To a tetrahydrofuran solution (20 mL) of 4.560 g (20 mmol) of p-(methanesulfonyloxy)propiophenone, a hexane solution (5 mL) of 3.516 g (1.1 equivalent) of bromine was added at 15° C., followed by 1 hour of stirring. To the resulting solution, 30 mL of saturated sodium hydrogen carbonate and 30 mL of ethyl acetate were added to conduct extraction. The organic layer was washed with 20 mL of a saturated sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, and subjected to distillation under a reduced pressure to remove the solvent. 1-[4-(Methanesulfonyloxy)phenyl]-2-bromo-1-propanone was obtained as an yellow, oily substance (10.12 g, crude yield: 97%).

Workup

  1. extractionextraction
  2. washThe organic layer was washed with 50 mL of saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationsubjected to distillation under a reduced pressure
  5. customto remove the solvents
  6. customA white solid was obtained as a result
  7. customThis white solid was crystallized from 40 mL of ethyl acetate and 120 mL of hexane

Sources & evidence

ORD record
ord-0491aaff4ede4a3f800a71aafa82c1af
Source dataset
uspto-grants-2008_08
Patent number
US07408084B2

Reaction notes

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