Bromine → 2-Bromo-1-(2,3-dichloro-4-(2-isopropyl-phenylsulfanyl)-phenyl)-ethanone

HRID 1246832Notes

Reaction equation

HRID 1246832 reaction equation
[Br:1]Br.[Cl:3][C:4]1[C:9]([Cl:10])=[C:8]([S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH:18]([CH3:20])[CH3:19])[CH:7]=[CH:6][C:5]=1[C:21](=[O:23])[CH3:22]>O1CCOCC1>[Br:1][CH2:22][C:21]([C:5]1[CH:6]=[CH:7][C:8]([S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH:18]([CH3:20])[CH3:19])=[C:9]([Cl:10])[C:4]=1[Cl:3])=[O:23]

Participants

4

Reactant 2

HCID 24408BromineHCID 219067491-(2,3-Dichloro-4-(2-isopropyl-phenylsulfanyl)-phenyl)-ethanone

Product 1

HCID 219067782-Bromo-1-(2,3-dichloro-4-(2-isopropyl-phenylsulfanyl)-phenyl)-ethanone

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Then 2-bromo-1-(2,3-dichloro-4-(2-isopropyl-phenylsulfanyl)-phenyl)-ethanone 41 was prepared as follows. A solution of Br2 (50 mg) in dioxane (1.0 ml) was added to a solution of compound 40 (100 mg, 0.3 mmole) in 2 ml of dioxane. The solution was then stirred for another 10 minutes and concentrated. The residue was dissolved in EtOAc and purified on a 5-g silica gel cartridge, giving the desired product 41 as a white solid. 136 mg, ˜100%. 1H-NMR (CDCl3, 500 MHz) δ 1.19 (d, J=8.5 Hz, 6H), 3.43 (heptet, J=8.5 Hz, 1H), 4.45 (s, 2H), 6.42 (d, J=8.4 Hz, 1H), 7.19 (d, J=8.4 Hz, 1H), 7.25–7.31 (m, 1H), 7.49–7.54 (m, 3H); MS (DCI/NH3) m/z 436 (M+NH4)+.

Workup

  1. customThen 2-bromo-1-(2,3-dichloro-4-(2-isopropyl-phenylsulfanyl)-phenyl)-ethanone 41 was prepared
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in EtOAc
  4. custompurified on a 5-g silica gel cartridge

Sources & evidence

ORD record
ord-4c1e07158f8d471fa65cbaaf6aafe0ee
Source dataset
uspto-grants-2006_10
Patent number
US07129247B2

Reaction notes

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