Diethyl Ether → 4-Methoxybenzenethiol

HRID 1601648Notes

Reaction equation

HRID 1601648 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 mmole) was added to a solution of the crude thiochromone (20 g, prepared in Example 77 above) in THF (100 mL) with cooling to 10° C. The reaction mixture was then allowed to rise to room temperature and stirred for 6 hours. The resultant mixture was 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 salt (18.5 g, 55% yield over three steps from 4-methoxybenzene thiol).

Workup

  1. customto rise 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-90ae2a30648247e9ae26a83519e4c445
Source dataset
uspto-grants-1999_11
Patent number
US05977351

Reaction notes

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