1,4-Dibromobenzene → 4-(2-(4-Bromophenyl)propan-2-yl)morpholine

HRID 447392Notes

Reaction equation

HRID 447392 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([Br:9])=[CH:5][CH:4]=1.[CH3:10][C:11]([N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)(C)[C:12]#N>C1COCC1>[Br:9][C:6]1[CH:7]=[CH:8][C:3]([C:11]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)([CH3:12])[CH3:10])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 78041,4-DibromobenzeneHCID 24237842-Methyl-2-(morpholin-4-yl)propanenitrileHCID 5462224Magnesium

Product 1

HCID 667303824-(2-(4-Bromophenyl)propan-2-yl)morpholineYield 10.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Magnesium turnings (190 mg, 7.4 mmol) was added to dry THF (15 mL) under argon. 1,4-dibromobenzene (2.43 g, 10.3 mmol) was added and the solution was heated to reflux for 30 min 2-Methyl-2-morpholinopropanenitrile (1 g, 6.6 mmol) was dissolved into THF (30 mL) and added dropwise to the solution at reflux. The mixture was stirred for 2 h and cooled to rt. The reaction was quenched with sat. K2CO3 solution and extracted with CH2Cl2 (200 mL), dried over MgSO4 and concentrated to an orange oil. The crude mixture was purified on a Biotage silica column (2-15% MeOH in CH2Cl2) to give the title compound as a yellow oil (204 mg, 10%). MS ESI 284.0, 286.0 [M+H]+, calcd for [C13H18BrNO+H]+ 284.1, 286.1.

Workup

  1. temperaturethe solution was heated
  2. additionadded dropwise to the solution
  3. temperatureat reflux
  4. customThe reaction was quenched with sat. K2CO3 solution
  5. extractionextracted with CH2Cl2 (200 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated to an orange oil
  8. customThe crude mixture was purified on a Biotage silica column (2-15% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-6c90c2185ea34af193a566797f6b5c07
Source dataset
uspto-grants-2013_07
Patent number
US08481533B2

Reaction notes

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