Benzyl Bromide → 1-(5-Benzenesulfonyl-2-benzyloxy-phenyl)-ethanone

HRID 2221309Notes

Reaction equation

HRID 2221309 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]1([S:15]([C:18]2[CH:19]=[CH:20][C:21]([OH:27])=[C:22]([C:24](=[O:26])[CH3:25])[CH:23]=2)(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(OCC)(=O)C>[C:9]1([S:15]([C:18]2[CH:19]=[CH:20][C:21]([O:27][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[C:22]([C:24](=[O:26])[CH3:25])[CH:23]=2)(=[O:17])=[O:16])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 189877381-(5-Benzenesulfonyl-2-hydroxy-phenyl)-ethanone

Product 1

HCID 597108891-(5-Benzenesulfonyl-2-benzyloxy-phenyl)-ethanone

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Benzyl bromide (1.443 g; 0.0087 mol) was added to a suspension of 1-(5-benzenesulfonyl-2-hydroxy-phenyl)-ethanone (2.01 g; 0.0073 mol) and potassium carbonate (2.01 g; 0.015 mol) in acetonitrile (5.0 mL). The mixture was heated under reflux for 18 hours. After cooling to ambient temperature, the mixture was diluted with ethyl acetate, filtered, washed with water and saturated sodium bicarbonate, dried (Na2SO4) and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel (hexane-ethyl acetate; 7:3) to give 1-(5-benzenesulfonyl-2-benzyloxy-phenyl)-ethanone as a white solid (2.17 g; 81%). A sample was recrystallized from diethyl ether-hexane: M. p. 80.5-82.4° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 18 hours
  3. filtrationfiltered
  4. washwashed with water and saturated sodium bicarbonate
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by flash chromatography on silica gel (hexane-ethyl acetate; 7:3)

Sources & evidence

ORD record
ord-ef375f39f8d346e6ac431d2c720e5c62
Source dataset
uspto-grants-2008_05
Patent number
US07368567B2

Reaction notes

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