4-Fluorothiophenol → HCID 20314601, compound

HRID 2419850Notes

Reaction equation

HRID 2419850 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.C[O-].[Na+].Br[CH2:13][CH2:14][C:15]([O:17]CC)=O.Cl.[NH2:21][OH:22]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:13][CH2:14][C:15]([NH:21][OH:22])=[O:17])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 677894-FluorothiophenolHCID 68320Ethyl 3-bromopropionateHCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium Methoxide2×

Product 1

HCID 20314601HCID 20314601, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

10 g (0.078 mol) of p-fluorothiophenol are added to a solution of 4.5 g (0.083 mol) of sodium methylate in 25 ml of methanol, and a solution of 14.5 g (0.08 mol) of ethyl 3-bromopropionate in 20 ml of methanol is then added dropwise. The mixture is heated for 2 hours to the reflux temperature, the alcohol is evaporated in vacuo, the residue is taken up in ether, the ether solution is washed with water and dried, and the ether is evaporated. The residue is treated, for 24 hours at 20° C, with a solution of hydroxylamine in methanol prepared from 7.7 g (0.11 mol) of hydroxylamine hydrochloride and 12 g (0.22 mol) of sodium methylate in 150 ml of methanol. The methanol is evaporated in vacuo, 200 ml of water are added, the mixture is extracted with ether and the hydroxamic acid is precipitated with concentrated HCl. It is filtered off, washed with water and dried. 10 g (62%) are obtained. Melting point = 93° C.

Workup

  1. temperatureThe mixture is heated for 2 hours to the reflux temperature
  2. customthe alcohol is evaporated in vacuo
  3. washthe ether solution is washed with water
  4. customdried
  5. customthe ether is evaporated
  6. additionThe residue is treated, for 24 hours at 20° C, with a solution of hydroxylamine in methanol
  7. customThe methanol is evaporated in vacuo, 200 ml of water
  8. additionare added
  9. extractionthe mixture is extracted with ether
  10. customthe hydroxamic acid is precipitated with concentrated HCl
  11. filtrationIt is filtered off
  12. washwashed with water
  13. customdried
  14. custom10 g (62%) are obtained

Sources & evidence

ORD record
ord-c17e7f54433a41eb856d3cc8c7867783
Source dataset
uspto-grants-1978_08
Patent number
US04107438

Reaction notes

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