Benzyl Bromide → 5-Benzyloxy-3-chloroxanthone

HRID 1414564Notes

Reaction equation

HRID 1414564 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:17])[C:7]3[C:12]([O:13][C:14]=2[CH:15]=1)=[C:11]([OH:16])[CH:10]=[CH:9][CH:8]=3.[H-].[Na+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C)C=O>[CH2:20]([O:16][C:11]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:12]=1[O:13][C:14]1[CH:15]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[C:6]2=[O:17])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 23460502HCID 23460502, compound

Product 1

HCID 234605165-Benzyloxy-3-chloroxanthone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

The 3-chloro-5-hydroxyxanthone (11 g.) in dimethylformamide (50 ml.) is added to a suspension of sodium hydride (1.5 g.) in dimethylformamide (100 ml.). The mixture is stirred at room temperature for 15 minutes and benzyl bromide (6 ml.) is added dropwise. The mixture is poured into water/ice (600 ml.), extracted with chloroform and the chloroform extract dired with MgS04. Evaporation of the solvent gives a light-brown solid which is recrystallised from ethanol to give 5-benzyloxy-3-chloroxanthone, m.p. 154° C.

Workup

  1. extractionextracted with chloroform
  2. extractionthe chloroform extract dired with MgS04
  3. customEvaporation of the solvent
  4. customgives a light-brown solid which
  5. customis recrystallised from ethanol

Sources & evidence

ORD record
ord-bccdb3a4c5f5462aae1e04fab8807a18
Source dataset
uspto-grants-1977_01
Patent number
US04001419

Reaction notes

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