Benzyl Bromide → HCID 10195119, compound

HRID 1767195Notes

Reaction equation

HRID 1767195 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:22])=[C:6]([C:8]2[CH2:12][CH2:11][CH2:10][C:9]=2[C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=2)[C:16]([OH:18])=[O:17])[CH:7]=1.[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[OH-].[K+]>CS(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:6]([C:8]2[CH2:12][CH2:11][CH2:10][C:9]=2[C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=2)[C:16]([OH:18])=[O:17])[CH:7]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 21112938HCID 21112938, compound

Product 1

HCID 10195119HCID 10195119, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

3-{2-[5-Bromo-2-(hydroxy)-phenyl]-cyclopent-1-enyl}-benzoic acid (0.04 g, 0.12 mmol), benzyl bromide (0.038 g, 0.22 moles), potassium hydroxide (˜0.15 g), in dimethyl sulphoxide (1.5 mL) were stirred at room temperature over 8 hrs under nitrogen. The reaction mixture was then quenched with ice/water (10/10 mL), stirred at room temperature for ˜1.5 hrs, acidified with 2N hydrochloric acid to pH˜3 and extracted with dichloromethane. The organic extract was then dried (magnesium sulphate) and concentrated down to an oil and was then chromatographed on Waters sep-pak cartridge (10 g) giving (0.028 g, 54%).

Workup

  1. customThe reaction mixture was then quenched with ice/water (10/10 mL)
  2. extractionextracted with dichloromethane
  3. extractionThe organic extract
  4. dry with materialwas then dried (magnesium sulphate)
  5. concentrationconcentrated down to an oil
  6. customwas then chromatographed on Waters sep-pak cartridge (10 g)
  7. customgiving (0.028 g, 54%)

Sources & evidence

ORD record
ord-f237dc07b6c74dfebebeadfbdc48ceed
Source dataset
uspto-grants-2007_06
Patent number
US07232821B2

Reaction notes

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