2-Bromo-1-(2-chloro-4-methoxy-5-methylphenyl)-1-propanone → HCID 9910112, compound

HRID 1178551Notes

Reaction equation

HRID 1178551 reaction equation
Br[CH:2]([CH3:15])[C:3]([C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([O:12][CH3:13])=[CH:7][C:6]=1[Cl:14])=O.[Cl:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:18]=1[C:24]1([C:27](=[S:29])[NH2:28])[CH2:26][CH2:25]1>CN(C)C=O.C(OCC)(=O)C>[Cl:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:18]=1[C:24]1([C:27]2[S:29][C:2]([CH3:15])=[C:3]([C:5]3[CH:10]=[C:9]([CH3:11])[C:8]([O:12][CH3:13])=[CH:7][C:6]=3[Cl:14])[N:28]=2)[CH2:26][CH2:25]1

Participants

5

Reactant 2

HCID 185078282-Bromo-1-(2-chloro-4-methoxy-5-methylphenyl)-1-propanoneHCID 87870424HCID 87870424, compound

Product 1

HCID 9910112HCID 9910112, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

2-Bromo-1-(2-chloro-4-methoxy-5-methly-phenyl)-propan-1-one (254 mg, 0.87 mmol) and 1-(2-Chloro-6-fluoro-phenyl) cyclopropane carbothioic acid amide (200 mg, 0.87) mmol) were dissolved in dimethlyformamide (DMF) (2.9 mL). The reaction was heated with stirring to 80° C. overnight. The mixture was then cooled, diluted with ethyl acetate and washed three times with water and once with brine. The organic layer was separated, dried with sodium sulfate and concentrated in vacuo. The crude product was then chromatographed on silica using an ethyl acetate/hexane gradient resulting in a pale green-yellow solid. Yield: 110 mg (18%). [MH]+422.0. 1H NMR (300 MHz, CDCl3) •1.54 (m, cyclopropyl, 2H), 2.11 (m, cyclopropyl, 2H), 2.27 (s, CH3, 3H), 2.28 (s, CH3, 3H), 3.93 (s, —OCH3, 3H), 6.97 (s, Ar, 1H), 7.15 (m, Ar, 1H), 7.35 (s, Ar, 1H), 7.37 (m, Ar, 2H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureThe mixture was then cooled
  3. washwashed three times with water
  4. customThe organic layer was separated
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe crude product was then chromatographed on silica using an ethyl acetate/hexane gradient
  8. customresulting in a pale green-yellow solid

Sources & evidence

ORD record
ord-d034e8da6bdd4f61af5157566659fa21
Source dataset
uspto-grants-2007_10
Patent number
US07276526B2

Reaction notes

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