Aluminum(III) Chloride → HCID 58245834, compound

HRID 424395Notes

Reaction equation

HRID 424395 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]([C:9](=[CH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:8])=[CH:4][CH:3]=1.[Cl-].[Cl-].[Cl-].[Al+3]>[N+](CC)([O-])=O>[Br:1][C:2]1[S:6][C:5]2[C:7](=[O:8])[CH:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:15]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 66702189HCID 66702189, compound

Product 1

HCID 58245834HCID 58245834, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 6587NitroethaneSolvent

Procedure

A solution of ethyl 2-(5-bromothiophene-2-carbonyl)-3-phenylacrylate (1.3 g, 3.56 mmol) and aluminum trichloride (0.563 g, 4.27 mmol) in nitroethane (20 ml) was heated at 83° C. for 2.75 hours. The reaction mixture was poured into 1N HCl-ice solution, and extracted with ethyl acetate. The organic phase was washed with brine, dried (MgSO4) and concentrated to give a brown oil. The crude product was purified by silica gel flash chromatography using 0-5% ethyl acetate in hexanes to give ethyl 2-bromo-6-oxo-4-phenyl-5,6-dihydro-4H-cyclopenta[b]thiophene-5-carboxylate as a viscous foam (1.024 g, 78.8% yield). LCMS m/z 366, 368 (M+1); 388.9, 386.9 (M+23); HPLC: Rt 3.438, 3.718 min.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customto give a brown oil
  6. customThe crude product was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-f7391e39322c41d191880823a601a2f1
Source dataset
uspto-grants-2012_01
Patent number
US08106046B2

Reaction notes

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