Benzyl Bromide → HCID 11190472, compound

HRID 585781Notes

Reaction equation

HRID 585781 reaction equation
[OH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9]([OH:17])[CH:10]=[CH:11][CH:12]=3)[O:7][C:6]=2[C:5]([CH2:18][CH:19]=[CH2:20])=[C:4]([OH:21])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CN(C=O)C.C(OCC)(=O)C>[CH2:28]([O:21][C:4]1[CH:3]=[C:2]([OH:1])[C:15]2[C:14](=[O:16])[C:13]3[C:8]([O:7][C:6]=2[C:5]=1[CH2:18][CH:19]=[CH2:20])=[C:9]([O:17][CH2:18][C:5]1[CH:6]=[CH:15][CH:2]=[CH:3][CH:4]=1)[CH:10]=[CH:11][CH:12]=3)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 11403362HCID 11403362, compound

Product 1

HCID 11190472HCID 11190472, compoundYield 160.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of xanthone 5 (48 g, 168 mmol) in dry DMF was added potassium carbonate (46 g, 336 mmol) and benzyl bromide (90 g, 526 mmol) and the mixture was heated to 110° C. for 8 hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (1.4L) and the remaining potassium carbonate was destroyed with 2M Sulfuric acid. The organic layer was washed with brine (2×500 mL), dried over magnesium sulfate and concentrated in vacuo to afford the xanthone 6 as a solid (63 g, 135 mmol, 81%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe remaining potassium carbonate was destroyed with 2M Sulfuric acid
  3. washThe organic layer was washed with brine (2×500 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3a94f83fdb0d4bdc927aaa9497c397fe
Source dataset
uspto-grants-2005_08
Patent number
US06933396B2

Reaction notes

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