Bromine → Ethanone, 2-bromo-1-[4-(methylthio)phenyl]-2-phenyl-

HRID 482912Notes

Reaction equation

HRID 482912 reaction equation
[C:1]1([CH2:7][C:8]([C:10]2[CH:15]=[CH:14][C:13]([S:16][CH3:17])=[CH:12][CH:11]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:18]Br>C(Cl)Cl.CCOCC>[Br:18][CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:8]([C:10]1[CH:11]=[CH:12][C:13]([S:16][CH3:17])=[CH:14][CH:15]=1)=[O:9]

Participants

5

Reactant 2

HCID 24408BromineHCID 27600881-(4-(methylthio)phenyl)-2-phenylethanone

Product 1

HCID 11336208Ethanone, 2-bromo-1-[4-(methylthio)phenyl]-2-phenyl-Yield 94.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 30 g (0.12 mole) of 2-phenyl-1-(4-methylthiophenyl)ethanone in 45 ml of methylene chloride and 450 ml of ether was added dropwise a solution of 20.8 g (0.13 mole) of bromine in 65 ml of methylene chloride. The reaction mixture decolorized and became slightly exothermic. After stirring an additional 30 minutes, the reaction mixture was concentrated under vacuum. The crystalline product was collected by filtration and washed with hexane to give 36.3 g (91.5%) of 2-bromo-2-phenyl-1-(4-methylthiophenyl)ethanone as an off-white solid, m.p. 101°-103°.

Workup

  1. concentrationthe reaction mixture was concentrated under vacuum
  2. filtrationThe crystalline product was collected by filtration
  3. washwashed with hexane

Sources & evidence

ORD record
ord-e728a761dbb645189b054173295207c2
Source dataset
uspto-grants-1986_03
Patent number
US04576958

Reaction notes

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