4-Bromotoluene → HCID 22418044, compound

HRID 1728568Notes

Reaction equation

HRID 1728568 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[Mg].Cl[C:11]1[CH:16]=[CH:15][C:14]([C:17]2[O:18][CH2:19][C:20]([CH3:23])([CH3:22])[N:21]=2)=[C:13](OC)[CH:12]=1.[Cl-:26].[NH4+]>C1COCC1>[Cl:26][C:16]1[CH:11]=[CH:12][C:13]([C:2]2[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=2)=[C:14]([C:17]2[O:18][CH2:19][C:20]([CH3:23])([CH3:22])[N:21]=2)[CH:15]=1

Participants

6

Reactant 4

HCID 78054-BromotolueneHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 22418036HCID 22418036, compound

Product 1

HCID 22418044HCID 22418044, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A THF solution (450 ml) of 46.0 g of 4-bromotoluene was dropwise added to 6.38 g of magnesium in a nitrogen stream. After heating under reflux for 40 min, the reaction mixture was dropwise added at room temperature to a THF solution (260 ml) of 30 g of 2-(4-chloro-2-methoxyphenyl)-4,4-dimethyloxazoline. The mixture was stirred at room temperature for 2 hr and then cooled, and an aqueous ammonium chloride was added thereto. The mixture was extracted with ethyl acetate, and the extract was washed with a dilute sodium hydroxide solution and a saline solution, dried over anhydrous magnesium sulfate and then concentrated to prepare 38 g of the title compound in a crude form.

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 40 min
  3. temperaturecooled
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe extract was washed with a dilute sodium hydroxide solution
  6. dry with materiala saline solution, dried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customto prepare 38 g of the title compound in a crude form

Sources & evidence

ORD record
ord-4d3f96f9f0eb46dc82ef7bc0338b9567
Source dataset
uspto-grants-1994_07
Patent number
US05328911

Reaction notes

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