Hydrochloric Acid → 3-Methyl-2-phenylthiophene

HRID 2231278Notes

Reaction equation

HRID 2231278 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH3:7].[C:8]1([Mg]Br)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl>C(OCC)C>[CH3:7][C:6]1[CH:5]=[CH:4][S:3][C:2]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 843142-Bromo-3-methylthiopheneHCID 178418255HCID 178418255, compound

Product 1

HCID 104196813-Methyl-2-phenylthiophene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

A stirred mixture of 2-bromo-3-methylthiophene (15.0 g, 0.085 mole) and bis(1,3-diphenylphosphino)propane nickel(II) chloride (0.5 g, 0.009 mole) in diethyl ether (75 mL) was cooled to 0° C. Phenyl magnesium bromide (29.6 mL of a 3M solution in diethyl ether) was added slowly, causing the reaction mixture to reflux. After complete addition, reflux was continued for 15 minutes. The mixture was cooled, and approximately 100 mL of an aqueous 10% hydrochloric acid solution was added. The resultant mixture was extracted with diethyl ether, and the extract was washed with an aqueous saturated sodium bicarbonate solution. The washed extract was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure yielding 17.3 g of 3-methyl-2-phenylthiophene as a colorless oil.

Workup

  1. temperatureto reflux
  2. additionAfter complete addition
  3. temperaturereflux
  4. temperatureThe mixture was cooled
  5. extractionThe resultant mixture was extracted with diethyl ether
  6. washthe extract was washed with an aqueous saturated sodium bicarbonate solution
  7. extractionThe washed extract
  8. dry with materialwas dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-54dab1588fa4438292276f99f4aeec1a
Source dataset
uspto-grants-1988_11
Patent number
US04782079

Reaction notes

Loading…