Water → HCID 12531898, compound

HRID 1863344Notes

Reaction equation

HRID 1863344 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C[O-].[Na+].Br[CH:13]([C:18]1[CH:23]=[CH:22][C:21]([S:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)=[CH:20][CH:19]=1)[C:14]([O:16][CH3:17])=[O:15].O>CO.C1C=CC=CC=1.[I-].[K+]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:13]([C:18]2[CH:23]=[CH:22][C:21]([S:24][C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=3)=[CH:20][CH:19]=2)[C:14]([O:16][CH3:17])=[O:15])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 962WaterHCID 97324-FluorophenolHCID 10942334Sodium MethoxideHCID 20392605HCID 20392605, compound

Product 1

HCID 12531898HCID 12531898, compoundYield 65.8%

Reagents, catalysts & solvents 3

HCID 4875Potassium IodideCatalystHCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

To a solution of 2.8 g of p-fluorophenol, 1.19 g of sodium methoxide and 50 mg of potassium iodide in 40 ml of methanol was added 7.43 g of methyl α-bromo-α-[p-(p-chlorophenylthio)phenyl]acetate in 10 ml of benzene. The mixture was refluxed overnight and then cooled to room temperature. The mixture was poured into 100 ml of water and extracted with 2×75 ml of ether. The combined extracts were washed with 50 ml of 5% NaOH, 50 ml water, saturated brine, and dried (MgSO4). Evaporation of the solvent at reduced pressure afforded an amber oil, which was chromatographed on 100 g of silica gel (benzene). Concentration of the eluate yielded an amber oil which crystallized on trituration with 100 ml of petroleum ether, mp 84.5°-86.5° C. (weight 6.05 g). Recrystallization from 50 ml of hexane yielded 5.3 g of a white solid, mp 84.5°-87° C.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. extractionextracted with 2×75 ml of ether
  3. washThe combined extracts were washed with 50 ml of 5% NaOH, 50 ml water, saturated brine
  4. dry with materialdried (MgSO4)
  5. customEvaporation of the solvent at reduced pressure
  6. customafforded an amber oil, which
  7. customwas chromatographed on 100 g of silica gel (benzene)
  8. customConcentration of the eluate yielded an amber oil which
  9. customcrystallized on trituration with 100 ml of petroleum ether, mp 84.5°-86.5° C. (weight 6.05 g)
  10. customRecrystallization from 50 ml of hexane

Sources & evidence

ORD record
ord-97a06fa66e574938bc7eba49fb625a32
Source dataset
uspto-grants-1979_09
Patent number
US04168385

Reaction notes

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