Bromine → HCID 57007269, compound

HRID 481413Notes

Reaction equation

HRID 481413 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:11]2[O:12][C:13]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:14]=3[CH:15]=2)[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].[Br:21]Br>C(Cl)(Cl)(Cl)Cl.ClCl>[CH2:1]([O:3][C:4]([C:6]1([C:11]2[O:12][C:13]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:14]=3[C:15]=2[Br:21])[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 24408BromineHCID 571071641-(5-Methylbenzofuran-2-yl)cyclopentane carboxylic acid ethyl ester2×

Product 1

HCID 57007269HCID 57007269, compound

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 24526ChlorineSolvent

Procedure

To a solution of product of Step 4, above (58) (1.0 mmol) in 2 ml CCl4 was added bromine (1.0 mmol) at ambient temperature and the reaction mixture was stirred for 2 hours, refluxed for 1 hour to ensure completion of the reaction, cooled to ambient temperature, diluted with CH2 Cl2 and washed with saturated sodium bicarbonate and brine. The combined organics were dried over MgSO4, filtered and concentrated to dryness. The crude residue was chromatographed on silica gel using 5% EtOAc in hexanes as the eluant to obtain the title compound (59).

Workup

  1. temperaturerefluxed for 1 hour
  2. customcompletion of the reaction
  3. washwashed with saturated sodium bicarbonate and brine
  4. dry with materialThe combined organics were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe crude residue was chromatographed on silica gel using 5% EtOAc in hexanes as the eluant

Sources & evidence

ORD record
ord-cff73398861347449708487d2281fa54
Source dataset
uspto-grants-1998_08
Patent number
US05789415

Reaction notes

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