Trimethylsilyldiazomethane → Methyl 4-(1-bromoethyl)benzoate

HRID 1631921Notes

Reaction equation

HRID 1631921 reaction equation
[Br:1][CH:2]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)[CH3:3].[CH3:13][Si](C=[N+]=[N-])(C)C>C(OCC)C.CO>[CH3:13][O:9][C:8](=[O:10])[C:7]1[CH:11]=[CH:12][C:4]([CH:2]([Br:1])[CH3:3])=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 51462254-(1-Bromoethyl)benzoic acid

Product 1

HCID 12342351Methyl 4-(1-bromoethyl)benzoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 4-(1-bromo-ethyl)-benzoic acid (2.70 g, 11.8 mmol) in diethyl ether (20 mL) and methanol (5 mL) was cooled to 0° C. and treated with trimethylsilyldiazomethane (2 M in diethylether, 11.8 mL). After 1 h at 0° C. the solvents were removed under reduced pressure, the residue was re-dissolved in ethyl acetate (20 mL) and washed with aqueous NaHCO3 solution. The organic layer was collected, dried over MgSO4 and evaporated under reduced pressure.

Workup

  1. customAfter 1 h at 0° C. the solvents were removed under reduced pressure
  2. dissolutionthe residue was re-dissolved in ethyl acetate (20 mL)
  3. washwashed with aqueous NaHCO3 solution
  4. customThe organic layer was collected
  5. dry with materialdried over MgSO4
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-de3b26a00daf40f5a9992d1f1d4019f3
Source dataset
uspto-grants-2014_07
Patent number
US08791272B2

Reaction notes

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