Potassium Carbonate → Benzoic acid, 3-[2-[2-(phenylmethoxy)phenyl]-1-cyclopenten-1-yl]-

HRID 1767188Notes

Reaction equation

HRID 1767188 reaction equation
C([O:3][C:4](=[O:17])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[CH2:15][CH2:14][CH2:13][C:12]=2Br)[CH:6]=1)C.C(=O)([O-])[O-].[K+].[K+].[CH2:24]([O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1B(O)O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(COC)OC>[CH2:24]([O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[C:12]1[CH2:13][CH2:14][CH2:15][C:11]=1[C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=1)[C:4]([OH:3])=[O:17])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2773253(2-(Benzyloxy)phenyl)boronic acidHCID 578620843-(2-Bromo-cyclopent-1-enyl)benzoic Acid Ethyl Ester

Product 1

HCID 10215735Benzoic acid, 3-[2-[2-(phenylmethoxy)phenyl]-1-cyclopenten-1-yl]-

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

3-(2-Bromo-cyclopent-1-enyl] benzoic acid ethyl ester (0.148 g, 0.0005 mol), tetrakis-triphenylphosphine palladium (o) (30 mg), potassium carbonate (0.200 g) and (2-benzyloxyphenyl) boronic acid (0.110 g, 0.5 mmol) in dimethoxyethane (5 mL) were refluxed for 17 h under nitrogen. The reaction mixture was then filtered through Keiselghur and evaporated down to an oil. Purification was carried out on a Waters separation pack (10 g) cartridge with dichloromethane/iso hexane giving the product (120 mg).

Workup

  1. filtrationThe reaction mixture was then filtered through Keiselghur
  2. customevaporated down to an oil
  3. customPurification
  4. customwas carried out on a Waters separation pack (10 g) cartridge with dichloromethane/iso hexane giving the product (120 mg)

Sources & evidence

ORD record
ord-93839fd9af6b4943bf9cfef3ed4d28c5
Source dataset
uspto-grants-2007_06
Patent number
US07232821B2

Reaction notes

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