Methane → HCID 53719030, compound

HRID 2052363Notes

Reaction equation

HRID 2052363 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([C:8]2[S:12][C:11]3[S:13][C:14](C(O)=O)=[CH:15][C:10]=3[CH:9]=2)=[O:7])=[CH:4][CH:3]=1.C.O.Cl>N1C2C(=CC=CC=2)C=CC=1.[Cu]>[S:12]1[C:11]2[S:13][CH:14]=[CH:15][C:10]=2[CH:9]=[C:8]1[C:6]([C:5]1[CH:19]=[CH:20][C:2]([F:1])=[CH:3][CH:4]=1)=[O:7]

Participants

7

Reactant 4

HCID 297MethaneHCID 313Hydrochloric AcidHCID 962Water2×HCID 20377678HCID 20377678, compound

Product 1

HCID 53719030HCID 53719030, compoundYield 92.5%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7047QuinolineSolvent

Procedure

5-(4-Fluorobenzoyl)-thieno[2,3-b]thiophene-2-carboxylic acid (48.1 g) and copper powder (8.2 g) are suspended in quinoline (410 cc) and heated at the boiling point for 5 minutes. After cooling, decolourizing charcoal (0.5 g) is added to the reaction mixture which is then filtered. The solution obtained is added dropwise to a mixture of distilled water (620 cc) and a 12 N aqueous solution of hydrogen chloride (289 cc), cooled in an ice bath, the rate of addition being regulated in such a way that the temperature of the mixture remains below 10° C. Distilled water (500 cc) is added to the reaction mixture, which is stirred for a further 30 minutes in the ice bath, and then the resulting crystals are filtered off, washed four times with distilled water (total 2000 cc) and dried in air. Crude (4-fluorophenyl) (thieno[2,3-b]thien-2-yl) ketone (38.1 g), melting at 113° C., is thus obtained.

Workup

  1. temperatureheated at the boiling point for 5 minutes
  2. temperatureAfter cooling
  3. filtrationis then filtered
  4. customThe solution obtained
  5. additionthe rate of addition
  6. customremains below 10° C
  7. filtrationthe resulting crystals are filtered off
  8. washwashed four times with distilled water (total 2000 cc)
  9. customdried in air

Sources & evidence

ORD record
ord-ea29134bd88546de8a7550dbb1b7f239
Source dataset
uspto-grants-1980_01
Patent number
US04183944

Reaction notes

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