2-Bromotoluene → HCID 23048938, compound

HRID 2106668Notes

Reaction equation

HRID 2106668 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH3:9].[CH:10]1([C:13]([C:15]2[N:16]([CH3:20])[CH:17]=[CH:18][CH:19]=2)=[O:14])[CH2:12][CH2:11]1.[Cl-].[NH4+]>O1CCCC1>[CH:10]1([C:13]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[CH3:9])([C:15]2[N:16]([CH3:20])[CH:17]=[CH:18][CH:19]=2)[OH:14])[CH2:11][CH2:12]1

Participants

6

Reactant 4

HCID 72362-BromotolueneHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 23048980HCID 23048980, compound

Product 1

HCID 23048938HCID 23048938, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of magnesium turnings (1.72 g, 0.071 mole) in anhydrous tetrahydrofuran (20 ml), 2-bromotoluene (12.1 g, 0.071 mole) in tetrahydrofuran (100 ml) was added dropwise under nitrogen. The reaction mixture was heated at reflux for 1 h after the initial exotherm had subsided before cyclopropyl-(N-methylpyrrol-2-yl)ketone (7.1 g, 0.047 mole) (J. Org. Chem., (1971), 36, 2897; J.Org.Chem. (1980), 45, 3172) in anhydrous tetrahydrofuran (100 ml) was introduced. After heating the reaction mixture at reflux for 2 h it was left overnight at room temperature. Saturated, aqueous ammonium chloride solution (100 ml) was added, and the mixture was extracted with diethyl ether (3×200 ml). The combined extracts were dried (MgSO4) and the solvents evaporated. The residue was flash chromatografied on silica gel eluting with n-heptane/tetrahydrofuran (19:1) providing the title compound as a solid (10.9 g).

Workup

  1. additionwas added dropwise under nitrogen
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 1 h after the initial exotherm
  4. additionwas introduced
  5. temperatureAfter heating the reaction mixture
  6. temperatureat reflux for 2 h it
  7. extractionthe mixture was extracted with diethyl ether (3×200 ml)
  8. dry with materialThe combined extracts were dried (MgSO4)
  9. customthe solvents evaporated

Sources & evidence

ORD record
ord-e794300c6be94363bc08d445e21d1074
Source dataset
uspto-grants-1990_06
Patent number
US04931450

Reaction notes

Loading…