Hydrochloric Acid → HCID 12232923, compound

HRID 258893Notes

Reaction equation

HRID 258893 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[CH:5][CH:6]=1.[F:7][C:8]1[CH:16]=[CH:15][C:11]([C:12](Cl)=[O:13])=[CH:10][CH:9]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>O.C(Cl)Cl>[CH3:1][C:2]1[S:3][C:4]([C:12]([C:11]2[CH:15]=[CH:16][C:8]([F:7])=[CH:9][CH:10]=2)=[O:13])=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 111262-MethylthiopheneHCID 678794-Fluorobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 12232923HCID 12232923, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 29.5 parts of 2-methylthiophene, 39.65 parts of p-fluorobenzoyl chloride and 280 parts of methylene chloride are added portionwise 40 parts of aluminium chloride while keeping the temperature at 20° C (water-bath). Upon completion, stirring is continued for 4 hours at room temperature. The reaction mixture is poured onto crushed ice and 50 parts of hydrochloric acid, while stirring vigorously. The layers are separated and the aqueous phase is washed with chloroform. The organic layers are dried and evaporated. The residue is taken up in benzene and the latter is evaporated again. The residue solidifies on triturating in petroleumether. The solid product is filtered off and crystallized from ethanol at -20° C, yielding p-fluorophenyl 5-methyl-2-thienyl ketone; mp. 68° C.

Workup

  1. customat 20° C
  2. additionThe reaction mixture is poured
  3. stirringwhile stirring vigorously
  4. customThe layers are separated
  5. washthe aqueous phase is washed with chloroform
  6. customThe organic layers are dried
  7. customevaporated
  8. customthe latter is evaporated again
  9. customon triturating in petroleumether
  10. filtrationThe solid product is filtered off
  11. customcrystallized from ethanol at -20° C

Sources & evidence

ORD record
ord-e5b7a96b6e9c435e85d346a5dad76685
Source dataset
uspto-grants-1977_07
Patent number
US04035376

Reaction notes

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