p-Chlorothiophenol → HCID 15063573, compound

HRID 2419852Notes

Reaction equation

HRID 2419852 reaction equation
[Cl: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][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7815p-ChlorothiophenolHCID 76300Ethyl 4-bromobutyrateHCID 10942334Sodium Methoxide

Product 1

HCID 15063573HCID 15063573, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

14.5 g (0.1 mol) of p-chlorothiophenol are added at 0° C to a solution of 5.4 g (0.1 mol) of sodium methylate in 50 ml of methanol and thereafter 19.5 g (0.1 mol) of ethyl γ-bromobutyrate dissolved in 40 ml of methanol are added dropwise at 20° C, whilst stirring. The mixture is heated for 2 hours to the reflux temperature and is then evaporated in vacuo, the residue is extracted with ether, the extract is washed with water and dried, and the ether is evaporated. 24 g (93%) of a white oil are obtained.

Workup

  1. additionare added dropwise at 20° C
  2. temperatureThe mixture is heated for 2 hours to the reflux temperature
  3. customis then evaporated in vacuo
  4. extractionthe residue is extracted with ether
  5. washthe extract is washed with water
  6. customdried
  7. customthe ether is evaporated

Sources & evidence

ORD record
ord-5eaec1a7e75048e695c4c1addfac9932
Source dataset
uspto-grants-1978_08
Patent number
US04107438

Reaction notes

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