Potassium Carbonate → HCID 19807727, compound

HRID 1195592Notes

Reaction equation

HRID 1195592 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[OH:12].C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][CH:21]1[CH2:26][CH2:25][CH2:24][S:23][CH2:22]1>C(#N)C.[I-].[K+]>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[O:12][CH2:20][CH:21]1[CH2:26][CH2:25][CH2:24][S:23][CH2:22]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 158655Phenol, 2-chloro-4-fluoro-5-nitro-HCID 19807724HCID 19807724, compound

Product 1

HCID 19807727HCID 19807727, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

47.9 g (250 mmol) of 2-chloro-4-fluoro-5-nitrophenol, 34.6 g (250 mmol) of potassium carbonate, 1 g of potassium iodide and 58.5 g (300 mmol) of 3-bromomethyltetrahydrothiopyran in 500 ml of acetonitrile were refluxed for 5 hours. The mixture was cooled to 25° C. and filtered, the solvent was removed from the filtrate, the residue was taken up in methylene chloride, and the solution was washed with water, dried and concentrated. 22 g (29%) of 2-chloro-4-fluoro-5-nitro-1-(3-tetrahydrothiopyranylmethoxy)benzene (melting point 100° to 103° C.) were obtained.

Workup

  1. filtrationfiltered
  2. customthe solvent was removed from the filtrate
  3. washthe solution was washed with water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b5e331719ac84b16b22a4a915c32550e
Source dataset
uspto-grants-1992_05
Patent number
US05112383

Reaction notes

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