Triphenylarsine → 3-(2-Bromo-cyclopent-1-enyl)benzoic Acid Ethyl Ester

HRID 1767190Notes

Reaction equation

HRID 1767190 reaction equation
[Br:1][C:2]1[CH2:6][CH2:5][CH2:4][C:3]=1[Sn](C)(C)C.[CH2:11]([O:13][C:14](=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17](I)[CH:16]=1)[CH3:12].C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C)C=O>[CH2:11]([O:13][C:14](=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:3]2[CH2:4][CH2:5][CH2:6][C:2]=2[Br:1])[CH:16]=1)[CH3:12]

Participants

5

Reactant 3

HCID 11773TriphenylarsineHCID 143542Ethyl 3-iodobenzoateHCID 12586555(2-Bromo-1-cyclopenten-1-yl)trimethylstannane

Product 1

HCID 578620843-(2-Bromo-cyclopent-1-enyl)benzoic Acid Ethyl EsterYield 31%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(2-Bromo-cyclopent-1-enyl)trimethyl stannane (˜80% pure) (13.150 g, 43.7 mmol), ethyl-3-iodobenzoate (24.000 g, 87.4 mmol), triphenylarsine (4.000 g) and tris(dibenzylideneacetone)palladium (0) (1.500 g), were heated in dimethylformamide (20 mL) at 100° C., under nitrogen for 92 hours. The reaction mixture was then filtered through highflo, thoroughly washed with dichloromethane, reduced to an oil, and purified by chromatography with iso-hexane containing ether (2%–50%) to give the title compound (4.000 g, 28%).

Workup

  1. filtrationThe reaction mixture was then filtered through highflo
  2. washthoroughly washed with dichloromethane
  3. custompurified by chromatography with iso-hexane
  4. additioncontaining ether (2%–50%)

Sources & evidence

ORD record
ord-481c6a8300c24653828c10a1c5ab771a
Source dataset
uspto-grants-2007_06
Patent number
US07232821B2

Reaction notes

Loading…