4-Bromotoluene → 4,4-Dimethyl-2-(4'-methyl-2-biphenylyl)-2-oxazoline

HRID 53422

Reaction equation

HRID 53422 reaction equation
[Mg].BrC(Br)C.Br[C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=1.[CH3:14][C:15]1([CH3:28])[CH2:19][O:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2OC)=[N:16]1.[Cl-].[NH4+]>O1CCCC1>[CH3:14][C:15]1([CH3:28])[CH2:19][O:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=2)=[N:16]1

Participants

7

Reactant 5

HCID 78054-BromotolueneHCID 112011,1-DibromoethaneHCID 25517Ammonium ChlorideHCID 3331894,4-Dimethyl-2-(2-methoxyphenyl)oxazolineHCID 5462224Magnesium2×

Product 1

HCID 6883014,4-Dimethyl-2-(4'-methyl-2-biphenylyl)-2-oxazolineYield 85.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Tetrahydrofuran (200 ml) was added to 2.5 g (103 mmol) of flaky magnesium, followed by the addition of a small amount of dibromoethane under stirring. After the confirmation of bubbling, 13 ml (106 mmol) of 4-bromotoluene was dropwise added thereto. After the confirmation of the dissolution of the magnesium, the mixture was further stirred at room temperature for one hour. This reaction liquid was dropwise added to a solution of 10.0 g (48.7 mmol) of 4,4-dimethyl-2-(2'-methoxyphenyl)oxazoline in tetrahydrofuran (100 ml), followed by stirring for 12 hours. The reaction liquid was poured into a saturated aqueous solution of ammonium chloride, followed by the extraction with chloroform. After washing with water and drying, vacuum concentration was conducted. The residue was purified by silica gel column chromatography (a n-hexane/ethyl acetate system) to give 11.0 g of the title compound as a crystal (yield 85%). m.p.; 56°-59° C.

Workup

  1. customAfter the confirmation of bubbling
  2. stirringthe mixture was further stirred at room temperature for one hour
  3. customThis reaction liquid
  4. stirringby stirring for 12 hours
  5. customThe reaction liquid
  6. extractionfollowed by the extraction with chloroform
  7. washAfter washing with water
  8. customdrying
  9. concentrationvacuum concentration
  10. customThe residue was purified by silica gel column chromatography (a n-hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-c2dbefa41b844817bc4dce80250238a3
Source dataset
uspto-grants-1997_04
Patent number
US05618969

Linked notes

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