Sodium hydride → HCID 57584960, compound

HRID 2077520Notes

Reaction equation

HRID 2077520 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[H-].[Na+].Br[C:12]1[S:13][CH:14]=[C:15]([Br:17])[N:16]=1>CN(C=O)C>[Br:17][C:15]1[N:16]=[C:12]([S:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[S:13][CH:14]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 677894-FluorothiophenolHCID 27632972,4-Dibromo-1,3-thiazole

Product 1

HCID 57584960HCID 57584960, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

4-Fluorothiophenol (0.48 mL, 4.5 mmol) was dissolved in DMF (10 mL) and then chilled to 0° C. in an ice bath. NaH (0.14 g, 5.8 mmol) was added slowly to the mixture and it was allowed to stir under inert atmosphere. After 1 hour, 2,4-dibromothiazole (1.0 g, 4.1 mmol) was added to the mixture and the ice bath was removed. The resulting mixture was allowed to stir 3 hours under an inert atmosphere. The mixture was quenched with 1N NaOH and diluted with DCM. The aqueous layer was extracted three times with 4:1 DCM/MeOH, and the combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was purified by silica gel chromatography (1-10% EtOAc/hexanes) to give 4-bromo-2-(4-fluorophenylthio)thiazole (1.0 g, 84% yield) as a white solid. MS (ESI pos. ion) m/z: 290 (MH+, 79Br), 292 (MH+, 81Br). Calculated exact mass for C9H5BrFNS2: 289 (79Br), 291 (81Br).

Workup

  1. customthe ice bath was removed
  2. stirringto stir 3 hours under an inert atmosphere
  3. customThe mixture was quenched with 1N NaOH
  4. additiondiluted with DCM
  5. extractionThe aqueous layer was extracted three times with 4:1 DCM/MeOH
  6. dry with materialthe combined organic extracts were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude material was purified by silica gel chromatography (1-10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-ddfab028c9d441d5beac0bdfb753fa92
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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