Bromine → 1-Phenyl-2-bromo-2-(4-(methylthio)phenyl)ethanone

HRID 741680Notes

Reaction equation

HRID 741680 reaction equation
[C:1]1([C:7](=[O:17])[CH2:8][C:9]2[CH:14]=[CH:13][C:12]([S:15][CH3:16])=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:18]Br>C(Cl)(Cl)(Cl)Cl.C(Cl)(Cl)Cl>[C:1]1([C:7](=[O:17])[CH:8]([Br:18])[C:9]2[CH:10]=[CH:11][C:12]([S:15][CH3:16])=[CH:13][CH:14]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 220095571-Phenyl-2-(4-(methylthio)phenyl)ethanone

Product 1

HCID 194267911-Phenyl-2-bromo-2-(4-(methylthio)phenyl)ethanoneYield 74.7%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolvent2×HCID 6212ChloroformSolvent

Procedure

To a solution of the product of step 1 (60 g, 246 mmol) in CCl4 (900 mL) and CHCl3 (900 mL) was added dropwise a solution of Br2 (43.2 g, 270 mmol) in CCl4 (50 mL). After addition was completed, the mixture was concentrated to about 1/3 of its original volume. The mixture was washed with saturated NaHCO3 (500 mL) and Na2S2O8 (2×250 mL). The pale yellow solution was dried over Na2SO4 and concentrated to dryness. The residue was stirred in 10 % EtO2 /hexane for 20 h and filtered to give 59 g of the title compound.

Workup

  1. additionAfter addition
  2. concentrationthe mixture was concentrated to about 1/3 of its original volume
  3. washThe mixture was washed with saturated NaHCO3 (500 mL) and Na2S2O8 (2×250 mL)
  4. dry with materialThe pale yellow solution was dried over Na2SO4
  5. concentrationconcentrated to dryness
  6. filtrationfiltered

Sources & evidence

ORD record
ord-11a74845c617430d973eff78dfa1c6a2
Source dataset
uspto-grants-1996_09
Patent number
US05552422

Reaction notes

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