Diethyl Ether → 4-Methoxybenzenethiol

HRID 2396423Notes

Reaction equation

HRID 2396423 reaction equation
C[Mg]Br.O1C2[C:8](=CC=CC=2)[C:7](=[S:14])[CH:6]=[CH:5]1.F[B-](F)(F)F.[H+].C[CH2:22][O:23][CH2:24][CH3:25]>C1COCC1>[CH3:22][O:23][C:24]1[CH:25]=[CH:8][C:7]([SH:14])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 28118Tetrafluoroboric acidHCID 14119507HCID 14119507, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 127654-MethoxybenzenethiolYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
10 °C

Procedure

Methyl magnesium bromide (50 mL of a 3M solution in ether, 0.15 mmol) was added to a solution of the crude thiochromone (20 g, prepared in Part C above) in THF (100 mL) with cooling to 10° C. The reaction mixture was then allowed to warm to room temperature and stirred for 6 hours. The mixture was then added, with vigorous stirring, to tetrafluoroboric acid (125 mL of a 50% aqueous solution) which had been diluted with ice/water (600 mL). A yellow precipitate formed, which was collected by vacuum filtration, washed thoroughly with hexanes and dried under reduced pressure to yield the desired salt (18.5 g, 55% yield over three steps from the 4-methoxybenzene thiol). The structure of this compound was confirmed by mass spectroscopy and by 1H and 13C NMR spectroscopy.

Workup

  1. temperatureto warm to room temperature
  2. customA yellow precipitate formed
  3. filtrationwhich was collected by vacuum filtration
  4. washwashed thoroughly with hexanes
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-7cc4da292f964f27baa560dfe4bc10b4
Source dataset
uspto-grants-1996_02
Patent number
US05492795

Reaction notes

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