Potassium Carbonate → 3-[2-(2-Benzyloxy-5-chlorophenyl)cyclopent-1-enyl] benzoic acid ethyl ester

HRID 1767209Notes

Reaction equation

HRID 1767209 reaction equation
Br[C:2]1[CH2:6][CH2:5][CH2:4][C:3]=1Br.[CH2:8]([O:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=1B(O)O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:26](=[O:29])([O-])[O-:27].[K+].[K+].[C:32]1(C)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[CH2:39](O)[CH3:40]>C(OCC)C.O>[CH2:39]([O:27][C:26](=[O:29])[C:32]1[CH:33]=[CH:34][CH:35]=[C:36]([C:2]2[CH2:6][CH2:5][CH2:4][C:3]=2[C:17]2[CH:18]=[C:19]([Cl:22])[CH:20]=[CH:21][C:16]=2[O:15][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:37]=1)[CH3:40]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 41987402-Benzyloxy-5-chlorobenzeneboronic acidHCID 44385281,2-DibromocyclopenteneHCID 21863594Toluene ethanol

Product 1

HCID 695075793-[2-(2-Benzyloxy-5-chlorophenyl)cyclopent-1-enyl] benzoic acid ethyl esterYield 62%

Reagents, catalysts & solvents 1

HCID 21584184Diethylether waterSolvent

Procedure

A mixture of 1,2-dibromocyclopentene (1.72 g, 7.6 mmol), 2-benzyloxy-5-chlorophenylboronic acid (500 mg, 1.9 mmol), potassium carbonate (2.1 g, 15.2 mmol) and tetrakis (triphenyl phosphine)palladium(0) (220 mg, 0.19 mmol) was stirred and heated in 1:1 toluene/ethanol (15 ml) at 90° C. under nitrogen for 2 hours. After cooling the mixture was diluted with diethyl ether/water and the organic phase dried (magnesium sulphate), evaporated to dryness and the residue purified by chromatography on silica (2% ethyl acetate in iso-hexane then 10% dichloromethane in iso-hexane) to yield the title compound as a white solid (427 mg, 62%). 1H NMR (CDCl3) δ:1.99–2.07 (2H, m), 2.67–2.72 (2H, m), 2.76–2.81 (2H, m), 5.06 (2H, s), 6.85 (1H, d, J=9 Hz), 7.17–7.38 (7H, m).

Workup

  1. temperatureAfter cooling the mixture
  2. dry with materialthe organic phase dried (magnesium sulphate)
  3. customevaporated to dryness
  4. customthe residue purified by chromatography on silica (2% ethyl acetate in iso-hexane

Sources & evidence

ORD record
ord-0c67e001854640b08fae5163ea9d749a
Source dataset
uspto-grants-2007_06
Patent number
US07232821B2

Reaction notes

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