Trimethylsilyldiazomethane → Methyl 3-cyano-5-fluorobenzoate

HRID 1260889Notes

Reaction equation

HRID 1260889 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([F:12])[CH:11]=1)[C:6]([OH:8])=[O:7])#[N:2].[Si](C=[N+]=[N-])(C)(C)[CH3:14]>CO>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([F:12])[CH:11]=1)[C:6]([O:8][CH3:14])=[O:7])#[N:2]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 27579633-Cyano-5-fluorobenzoic acid

Product 1

HCID 26597287Methyl 3-cyano-5-fluorobenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(Step 1) To a solution of 3-cyano-5-fluorobenzoic acid (1.0 g) in methanol (20 ml) was added TMS diazomethane (2M diethyl ether solution, 5 ml) at 0° C., and the mixture was stirred for 1 hr. The reaction solution was quenched with water and diluted with ethyl acetate. The organic layer was washed with aqueous sodium hydrogen carbonate solution and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give methyl 3-cyano-5-fluorobenzoate (0.58 g).

Workup

  1. customThe reaction solution was quenched with water
  2. additiondiluted with ethyl acetate
  3. washThe organic layer was washed with aqueous sodium hydrogen carbonate solution
  4. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-bfa9a0aabde54aa189d5a0113b5e9160
Source dataset
uspto-grants-2013_06
Patent number
US08470859B2

Reaction notes

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