Hydrochloric Acid → HCID 12232925, compound

HRID 258890Notes

Reaction equation

HRID 258890 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[Cl:6][C:7]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:8]=1[C:9](Cl)=[O:10].Cl>C1C=CC=CC=1>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:9]([C:8]1[CH:12]=[CH:13][C:14]([F:16])=[CH:15][C:7]=1[Cl:6])=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8030ThiopheneHCID 27365462-Chloro-4-fluorobenzoyl chloride

Product 1

HCID 12232925HCID 12232925, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirred mixture of 25.25 parts of thiophene, 58.1 parts of 2-chloro-4-fluorobenzoyl chloride and 200 parts of anhydrous benzene are added dropwise 78.16 parts of stannic chloride (fuming) at room temperature (slightly exothermic reaction: the temperature is kept for 3 hours at 25° C). The reaction mixture is poured onto a mixture of crushed ice and concentrated hydrochloric acid solution. The while is stirred for a few minutes and the layers are separated. The organic layer is diluted with 80 parts of toluene, washed successively with 200 parts of sodium hydroxide solution 5% and with 200 parts of water, dried and evaporated. The residue is distilled, yielding 2-chloro-4-fluorophenyl 2-thienyl ketone; bp. 129°-130° C at 0.5 mm pressure.

Workup

  1. customslightly exothermic reaction
  2. customthe layers are separated
  3. additionThe organic layer is diluted with 80 parts of toluene
  4. washwashed successively with 200 parts of sodium hydroxide solution 5% and with 200 parts of water
  5. customdried
  6. customevaporated
  7. distillationThe residue is distilled

Sources & evidence

ORD record
ord-4d60764b5618450aaf845a645fd0ad14
Source dataset
uspto-grants-1977_07
Patent number
US04035376

Reaction notes

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