Toluene → 1-(1-Azido-1-methylethyl)-3-methoxybenzene

HRID 1373253Notes

Reaction equation

HRID 1373253 reaction equation
C1(C)C=CC=CC=1.[CH3:8][O:9][C:10]1[CH:11]=[C:12]([C:16](O)([CH3:18])[CH3:17])[CH:13]=[CH:14][CH:15]=1.C[Si]([N:24]=[N+:25]=[N-:26])(C)C>O>[N:24]([C:16]([C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([O:9][CH3:8])[CH:11]=1)([CH3:18])[CH3:17])=[N+:25]=[N-:26]

Participants

5

Reactant 3

HCID 1140TolueneHCID 78378AzidotrimethylsilaneHCID 5904222-(3-Methoxyphenyl)-2-propanol

Product 1

HCID 178157801-(1-Azido-1-methylethyl)-3-methoxybenzeneYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Boron trifluoride-diethyl ether complex (11.2 g, 78.9 mmols) was dropwise added to a toluene (100 ml) solution of 2-(3-methoxyphenyl)propan-2-ol (10.9 g, 65.6 mmols) and trimethylsilylazide (8.3 g, 72 mmols), at room temperature. The resulting mixture was stirred at room temperature for 20 hours. The reaction mixture was poured into water, and extracted with ethyl acetate. The extract was washed with brine, and then dried with anhydrous magnesium sulfate. This was concentrated under reduced pressure to give an oil of 1-(1-azido-1-methylethyl)-3-methoxybenzene (12.5 g, 100%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried with anhydrous magnesium sulfate
  4. concentrationThis was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9e4b1d47a623413fbc4e49a4dd56d2c5
Source dataset
uspto-grants-2007_01
Patent number
US07160887B1

Reaction notes

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