Diisopropylethylamine → 3-Fluoro-4-nitroanisole

HRID 638988Notes

Reaction equation

HRID 638988 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[CH:12](N(C(C)C)CC)(C)C.C[Si](C=[N+]=[N-])(C)C>C(#N)C.CO>[CH3:12][O:11][C:4]1[CH:5]=[CH:6][C:7]([N+:8]([O-:10])=[O:9])=[C:2]([F:1])[CH:3]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 167693TrimethylsilyldiazomethaneHCID 5209483-Fluoro-4-nitrophenol

Product 1

HCID 5656543-Fluoro-4-nitroanisoleYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 3-fluoro-4-nitrophenol (25 g, 0.159 mmol) in acetonitrile (500 mL) and methanol (500 mL) was treated with diisopropyl ethylamine (28 mL). The reaction mixture was cooled in an ice-bath and after 30 minutes, trimethylsilyldiazomethane was added dropwise. The mixture was stirred at room temperature for 18 hours then evaporated under vacuum to afford the product as an oil (29.4 g, 100%). MS (+ve ion electrospray) m/z 172 (MH+).

Workup

  1. temperatureThe reaction mixture was cooled in an ice-bath and after 30 minutes
  2. customthen evaporated under vacuum

Sources & evidence

ORD record
ord-94b73edbe72f48c0928b073b938adcee
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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