4-Methoxybenzenethiol → 1-(Cyclopropylthio)-4-methoxybenzene

HRID 1798804Notes

Reaction equation

HRID 1798804 reaction equation
[CH3:1][C:2]([CH3:5])([O-])C.[Na+].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([SH:15])=[CH:11][CH:10]=1.BrC1CC1>CCO>[CH:5]1([S:15][C:12]2[CH:13]=[CH:14][C:9]([O:8][CH3:7])=[CH:10][CH:11]=2)[CH2:2][CH2:1]1

Participants

5

Reactant 3

HCID 127654-MethoxybenzenethiolHCID 78037BromocyclopropaneHCID 23676156Sodium t-butoxide

Product 1

HCID 126929601-(Cyclopropylthio)-4-methoxybenzene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of sodium t-butoxide (317 mg, 3.3 mmol) in 15 mL EtOH at 0° C. was slowly added 4-methoxybenzenethiol (420 mg, 3 mmol). After completion of addition, the reaction was stirred at RT for 1 hour before cooling down to 0° C. Bromocyclopropane (417 mg, 3.45 mmol) was added slowly, and the mixture was brought to reflux for one hour, cooled and concentrated. Water (1 mL) was added and the mixture was extract with ethyl acetate. The organic phases were dried and purified by column chromatography eluting with 20% ethyl acetate/hexanes to give the desired product.

Workup

  1. customat 0° C.
  2. additionAfter completion of addition
  3. temperaturebefore cooling down to 0° C
  4. temperatureto reflux for one hour
  5. temperaturecooled
  6. concentrationconcentrated
  7. additionWater (1 mL) was added
  8. extractionthe mixture was extract with ethyl acetate
  9. customThe organic phases were dried
  10. custompurified by column chromatography
  11. washeluting with 20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-11809a4ef40a4ea9bbe8c6cff0dec5a1
Source dataset
uspto-grants-2013_01
Patent number
US08343990B2

Reaction notes

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