Benzyl Bromide → HCID 58913484, compound

HRID 1296957Notes

Reaction equation

HRID 1296957 reaction equation
[Cl:1][C:2]1[C:3]([OH:20])=[CH:4][C:5]([OH:19])=[C:6]([C:8](=[O:18])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(#N)C.O>[CH2:27]([O:19][C:5]1[CH:4]=[C:3]([O:20][CH2:8][C:6]2[CH:7]=[CH:2][CH:3]=[CH:4][CH:5]=2)[C:2]([Cl:1])=[CH:7][C:6]=1[C:8](=[O:18])[CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 11277788HCID 11277788, compound

Product 1

HCID 58913484HCID 58913484, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

1-(5-Chloro-2,4-dihydroxy-phenyl)-2-(4-methoxy-phenyl)-ethanone (1 eq) was dissolved in acetonitrile and potassium carbonate (4 eq) was added portion wise. The suspension was stirred for five minutes, before the addition of benzyl bromide (2.4 eq), and after which, the reaction mixture was stirred under nitrogen at reflux for 3 hours. The reaction was allowed to cool to room temperature and diluted with water. This was extracted into ethyl acetate. The organic phase was dried over MgSO4, filtered and concentrated in vacuo to give a syrup. This was triturated with 1:1 diethyl ether:hexane to give 1-(2,4-bis-benzyloxy-5-chloro-phenyl)-2-(4-methoxy-phenyl)-ethanone as a white solid.

Workup

  1. temperatureat reflux for 3 hours
  2. extractionThis was extracted into ethyl acetate
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a syrup
  7. customThis was triturated with 1:1 diethyl ether

Sources & evidence

ORD record
ord-1c21046a8a7a4ef9bb5c93385ee8fa15
Source dataset
uspto-grants-2007_07
Patent number
US07247734B2

Reaction notes

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