Benzyl Bromide → 2-Benzyloxy-2'-methoxybenzophenone

HRID 434205Notes

Reaction equation

HRID 434205 reaction equation
[OH:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH3:13])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CS(C)=O.C(OCC)C.O>[CH2:24]([O:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH3:13])=[O:5])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 100596522-Hydroxy-2'-methoxybenzophenone

Product 1

HCID 100872422-Benzyloxy-2'-methoxybenzophenone

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-hydroxy-2′-methoxybenzophenone (12) (8.08 g, 0.0354 mol), potassium carbonate (24.5 g, 0.177 mol) and benzyl bromide (4.4 mL, 0.037 mol) in 90 mL of dimethylsulfoxide was stirred overnight at room temperature. The resulting reaction mixture was diluted with diethyl ether and water and the aqueous layer was extracted with fresh diethyl ether. The combined organic layers were washed with water, followed by saturated NaCI and dried over sodium sulfate. After purification by flash column chromatography (silica gel, dichloromethane/hexanes eluent), 2-benzyloxy-2′-methoxybenzophenone (13) was obtained as a colorless oil.

Workup

  1. customThe resulting reaction mixture
  2. extractionthe aqueous layer was extracted with fresh diethyl ether
  3. washThe combined organic layers were washed with water
  4. dry with materialdried over sodium sulfate
  5. customAfter purification by flash column chromatography (silica gel, dichloromethane/hexanes eluent)

Sources & evidence

ORD record
ord-117d1fab71174ab0b06793af68c685ab
Source dataset
uspto-grants-2003_12
Patent number
US06670512B2

Reaction notes

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