Hydrochloric Acid → 3-Formyl-5-(pentafluoro-lambda6-sulphanyl)benzoic acid

HRID 1055656Notes

Reaction equation

HRID 1055656 reaction equation
CC([Mg]Cl)C.Br[C:7]1[CH:8]=[C:9]([CH:13]=[C:14]([S:16]([F:21])([F:20])([F:19])([F:18])[F:17])[CH:15]=1)[C:10]([OH:12])=[O:11].CN([CH:25]=[O:26])C.Cl>C(OCC)C.C1COCC1>[CH:25]([C:7]1[CH:8]=[C:9]([CH:13]=[C:14]([S:16]([F:21])([F:20])([F:19])([F:18])[F:17])[CH:15]=1)[C:10]([OH:12])=[O:11])=[O:26]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 58137421HCID 58137421, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 896999913-Formyl-5-(pentafluoro-lambda6-sulphanyl)benzoic acid

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

With ice bath cooling, 11.5 ml (23 mmol) of a 2 M solution of 2-propylmagnesium chloride in diethyl ether were added dropwise to a solution of 3.0 g (9.17 mmol) of the compound of Example 15A in 1.6 ml of abs. THF. After the addition had ended, stirring was continued without cooling for another 30 min 1.76 ml (22.9 mmol) of DMF were added with ice bath cooling, and the mixture was stirred without cooling for a further 30 min. 20 ml of 1 M hydrochloric acid were then added, and the mixture was extracted with 100 ml of ethyl acetate. The organic phase was washed with 1 M hydrochloric acid and saturated sodium chloride solution, dried over sodium sulphate, filtered and concentrated to dryness on a rotary evaporator. The residue was suspended in 50 ml of dichloromethane/pentane (1:1) and the solid was filtered off and dried. Any contaminations present were removed by preparative HPLC (Method 22). This gave 780 mg (31% of theory) of the title compound.

Workup

  1. temperatureWith ice bath cooling
  2. additionAfter the addition
  3. additionwere added with ice bath
  4. temperaturecooling
  5. stirringthe mixture was stirred
  6. temperaturewithout cooling for a further 30 min
  7. extractionthe mixture was extracted with 100 ml of ethyl acetate
  8. washThe organic phase was washed with 1 M hydrochloric acid and saturated sodium chloride solution
  9. dry with materialdried over sodium sulphate
  10. filtrationfiltered
  11. concentrationconcentrated to dryness on a rotary evaporator
  12. filtrationthe solid was filtered off
  13. customdried
  14. customAny contaminations present were removed by preparative HPLC (Method 22)

Sources & evidence

ORD record
ord-7148d4a50a7e457580c4ae6dad5edc45
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

Loading…