Trichloroacetyl chloride → 4,4-Dichloro-3-(4-methylthiophenyl)-2-phenyl-2-cyclobuten-1-one

HRID 399065Notes

Reaction equation

HRID 399065 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.[Cl:17][C:18](Cl)([Cl:22])[C:19](Cl)=[O:20]>CCOCC>[Cl:17][C:18]1([Cl:22])[C:19](=[O:20])[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:9]1[C:6]1[CH:7]=[CH:8][C:3]([S:2][CH3:1])=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 6420Trichloroacetyl chlorideHCID 15786867HCID 15786867, compound

Product 1

HCID 178815824,4-Dichloro-3-(4-methylthiophenyl)-2-phenyl-2-cyclobuten-1-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a suspension of l-(methylthio)-4-(phenylethynyl)benzene (method 6, 20 g) and Zn(Cu) couple (17.3 g) in anhydrous ether (450 mL) at 15° C. was added trichloroacetyl chloride (32.4 g) dropwise (over 3h). Internal temperature was maintained between 13°-16° C. during addition. The mixture was stirred at r.t. for 18 hr, filtered through a pad of celite®, washed with a saturated NH4Cl sol., saturated NaCHO3 sol., brine, dried (MgSO4) and the solvents evaporated. The resulting residue was first purified by flash chromatography (silica gel; hexane/EtOAc (98:2 to 90:10)) and then the resulting solid was stirred vigorously in Et2O for 3 hr and filtered to afford the title compound as a pale yellow solid, m.p. 99°-100° C.

Workup

  1. temperatureInternal temperature was maintained between 13°-16° C. during addition
  2. filtrationfiltered through a pad of celite®
  3. washwashed with a saturated NH4Cl sol., saturated NaCHO3 sol., brine
  4. dry with materialdried (MgSO4)
  5. customthe solvents evaporated
  6. customThe resulting residue was first purified by flash chromatography (silica gel; hexane/EtOAc (98:2 to 90:10))
  7. stirringthe resulting solid was stirred vigorously in Et2O for 3 hr
  8. filtrationfiltered

Sources & evidence

ORD record
ord-b4eecc152aa34740895347cea58f5169
Source dataset
uspto-grants-1998_10
Patent number
US05817700

Reaction notes

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