Thioanisole → 2-(4-Bromophenyl)-1-[4-(methylthio)phenyl]ethanone

HRID 396845Notes

Reaction equation

HRID 396845 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.[C:12]1([S:18][CH3:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Al+3].[Cl-].[Cl-].[Cl-]>S(Cl)(Cl)=O.CCOCC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([C:15]2[CH:16]=[CH:17][C:12]([S:18][CH3:19])=[CH:13][CH:14]=2)=[O:11])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 7520ThioanisoleHCID 74654Benzeneacetic acid, 4-bromo-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 114500672-(4-Bromophenyl)-1-[4-(methylthio)phenyl]ethanoneYield 52.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
90 °C

Procedure

4-Bromophenylacetic acid (10.8 g, 0.050 mol) was disolved in thionyl chloride (50 mL) and stirred for 30 min at 90° C. The mixture was concentrated and the residual oil was disolved in carbon disulfide (100 mL) and thioanisole (12.5 g, 0.10 mol) was added and the mixture was cooled to 0° C., and AlCl3 (14.7 g, 0.11 mol) was added portionwise. The mixture was stirred at room temperature for 16 h. The resultant dark green suspension was poured into ice water (150 mL) and extracted with CH2Cl2 (150 mL×2), washed with aqueous saturated NaHCO3 (50 mL), dried over MgSO4, and concentarted in vacuo gave the solid. The solid was suspended in ether and collected by filtration to give the title compound (8.4 g, 46%).

Workup

  1. concentrationThe mixture was concentrated
  2. temperaturethe mixture was cooled to 0° C.
  3. stirringThe mixture was stirred at room temperature for 16 h
  4. extractionextracted with CH2Cl2 (150 mL×2)
  5. washwashed with aqueous saturated NaHCO3 (50 mL)
  6. dry with materialdried over MgSO4
  7. customgave the solid
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-c8c67e69f21a4f7699ffd1a83791f999
Source dataset
uspto-grants-2003_08
Patent number
US06608095B2

Reaction notes

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