Benzene, 1-bromo-4-(trifluoromethyl)- → HCID 123151185, compound

HRID 2370766Notes

Reaction equation

HRID 2370766 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][CH:4]=1.[Br:13][C:14]1[C:15](/[CH:20]=[N:21]/[S@:22]([C:24]([CH3:27])([CH3:26])[CH3:25])=[O:23])=[N:16][CH:17]=[CH:18][CH:19]=1>C1COCC1>[Br:13][C:14]1[C:15]([CH:20]([NH:21][S@:22]([C:24]([CH3:27])([CH3:26])[CH3:25])=[O:23])[C:3]2[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][CH:4]=2)=[N:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-HCID 5462224MagnesiumHCID 89310313HCID 89310313, compound

Product 1

HCID 123151185HCID 123151185, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of magnesium (2.143 g, 88 mmol) in THF (50 mL), was added 4-bromobenzotrifluoride (5.06 mL, 36.2 mmol). Stirring was continued for 4 h (caution: slightly exothermic, cooled with a water bath if needed). The resulting mixture was added to a stirred solution of (S,E)-N-((3-bromopyridin-2-yl)methylene)-2-methylpropane-2-sulfinamide (5.1 g, 17.64 mmol) in THF (100 mL) at −78° C. in a dropwise fashion. The mixture was stirred for another hour after addition and the reaction was then quenched with saturated aqueous NH4Cl, extracted with Et2O (3×20 mL), dried over Na2SO4, concentrated, and purified by column chromatography using silica (100-200 mesh) with 5% EtOAc in hexane as eluent to give the title compound as a brown oil.

Workup

  1. temperature(caution: slightly exothermic, cooled with a water bath
  2. stirringThe mixture was stirred for another hour
  3. additionafter addition
  4. customthe reaction was then quenched with saturated aqueous NH4Cl
  5. extractionextracted with Et2O (3×20 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. custompurified by column chromatography

Sources & evidence

ORD record
ord-b8e63f25f3734826bcadb829b6985a8a
Source dataset
uspto-grants-2014_04
Patent number
US08710043B2

Reaction notes

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