Benzyl Bromide → HCID 69507873, compound

HRID 1767201Notes

Reaction equation

HRID 1767201 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([OH:25])=[C:9]([C:11]2[CH2:15][CH2:14][CH2:13][C:12]=2[C:16]2[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=2)[C:19]([OH:21])=[O:20])[CH:10]=1)(=[O:4])=[O:3].C(=O)([O-])[O-].[K+].[K+].[CH2:32](Br)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CC(C)=O.C(OCC)C.O>[CH2:32]([O:20][C:19](=[O:21])[C:18]1[CH:22]=[CH:23][CH:24]=[C:16]([C:12]2[CH2:13][CH2:14][CH2:15][C:11]=2[C:9]2[CH:10]=[C:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH:6]=[CH:7][C:8]=2[O:25][CH2:11][C:9]2[CH:10]=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:17]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 21112946HCID 21112946, compound

Product 1

HCID 69507873HCID 69507873, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 21584184Diethylether waterSolvent

Procedure

A stirred mixture of 3-{2-[5-methylsulfonyl-2-(hydroxy)- -phenyl]-cyclopent-1-enyl}-benzoic acid (65 mg, 0.2 mmol), potassium carbonate (138 mg, 1 mmol) and benzyl bromide (75 mg, 0.44 mmol) in acetone (4 ml) was refluxed for 16 hours then cooled and diluted with diethyl ether/water. The organic phase was dried (MgSO4), evaporated to dryness and purified using Biotage with ethyl acetate/iso-hexane (1:19) to yield the title compound as a colourless gum. (85 mg, 84%).

Workup

  1. temperaturewas refluxed for 16 hours
  2. temperaturethen cooled
  3. dry with materialThe organic phase was dried (MgSO4)
  4. customevaporated to dryness
  5. custompurified

Sources & evidence

ORD record
ord-fe5f2be6928b4e278974be6122580937
Source dataset
uspto-grants-2007_06
Patent number
US07232821B2

Reaction notes

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