2-Bromoanisole → 2-(2'-Methoxy-[1,1'-biphenyl]-2-yl)-4,4-dimethyl-2-oxazoline

HRID 354574

Reaction equation

HRID 354574 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[Mg]Br.BrC1C=CC=CC=1OC.[Mg].CO[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]1[O:30][CH2:31][C:32]([CH3:35])([CH3:34])[N:33]=1>C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]1[O:30][CH2:31][C:32]([CH3:35])([CH3:34])[N:33]=1

Participants

6

Reactant 4

HCID 113582-BromoanisoleHCID 3331894,4-Dimethyl-2-(2-methoxyphenyl)oxazolineHCID 5462224MagnesiumHCID 178489560HCID 178489560, compound

Product 1

HCID 126110122-(2'-Methoxy-[1,1'-biphenyl]-2-yl)-4,4-dimethyl-2-oxazolineYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-Methoxyphenylmagnesium bromide, prepared from 2-bromoanisole (22.4 g, 120 mmol) and magnesium (2.9 g, 120 mmol), in dry THF (75 ml) was added dropwise to a stirred solution of 2-(2-methoxyphenyl)-4,4-dimethyl-2-oxazoline (20.4 g, 100 mmol) in dry THF (150 ml) under N2 at 20° C. Stirring of the solution was continued for 20 hours and then the reaction mixture was quenched by the addition of saturated ammonium chloride solution. The resulting mixture was extracted with ether (2×500 ml), dried over MgSO4, filtered and evaporated. The residue was chromatographed on silica gel (ethyl acetate-hexane) to provide title compound as colorless crystals (25.3 g, 90%), mp 129°-131° C.

Workup

  1. customthe reaction mixture was quenched by the addition of saturated ammonium chloride solution
  2. extractionThe resulting mixture was extracted with ether (2×500 ml)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was chromatographed on silica gel (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-7aa77486be2f4976a415c984f8913fa5
Source dataset
uspto-grants-1983_03
Patent number
US04375475

Linked notes

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