Benzyl mercaptan → HCID 58349837, compound

HRID 2047906Notes

Reaction equation

HRID 2047906 reaction equation
[H-].[Na+].[C:3]1([CH2:9][SH:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][N:13]=1>O1CCCC1.O>[CH2:9]([S:10][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][N:13]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 7509Benzyl mercaptanHCID 24758Sodium hydrideHCID 27831712-Bromo-5-fluoropyridine

Product 1

HCID 58349837HCID 58349837, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of sodium hydride (60% in oil, 440 mg) in tetrahydrofuran (40 mL) was added dropwise phenylmethanethiol (1.37 g) at room temperature, 2-bromo-5-fluoropyridine (1.76 g) was added to the reaction mixture, and the mixture was stirred at 60° C. for 5 hr. The reaction mixture was diluted with water and concentrated under reduced pressure. The residual aqueous layer was extracted twice with ethyl acetate. Combined organic layers were washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane hexane-ethyl acetate=97:3) to give the title compound as a crude brown oil (yield 244 mg).

Workup

  1. concentrationconcentrated under reduced pressure
  2. extractionThe residual aqueous layer was extracted twice with ethyl acetate
  3. washCombined organic layers were washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: hexane hexane-ethyl acetate=97:3)

Sources & evidence

ORD record
ord-f43df4354cc94213aed613d00d669738
Source dataset
uspto-grants-2013_11
Patent number
US08592597B2

Reaction notes

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