Trimethylsilyldiazomethane → Methyl 3-fluoro-4-nitrobenzoate

HRID 1784297Notes

Reaction equation

HRID 1784297 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[F:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[N+:18]([O-:20])=[O:19])[C:12]([OH:14])=[O:13]>CO>[F:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=1[N+:18]([O-:20])=[O:19])[C:12]([O:14][CH3:1])=[O:13]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 2306533-Fluoro-4-nitrobenzoic acid

Product 1

HCID 592761Methyl 3-fluoro-4-nitrobenzoateYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of trimethylsilyldiazomethane (2M in hexane, 50 ml, 4 eq) is slowly added to a solution of 3-fluoro-4-nitrobenzoic acid (4.7 g, 1 eq) in methanol (70 ml) until the gas evolution ceases. The excess trimethylsilyldiazomethane is consumed by the dropwise addition of acetic acid until the solution becomes discoloured. The mixture is then concentrated under reduced pressure at a temperature of approximately 40° C. Water (200 ml) and dichloromethane (300 ml) are added to the residue. After decantation and extractions, the combined organic phases are washed with salt water, dried over Na2SO4 then concentrated under reduced pressure at 40° C. The solid obtained is washed with petroleum ether and dried (4.4 g; 87% yield).

Workup

  1. customThe excess trimethylsilyldiazomethane is consumed by the dropwise addition of acetic acid until the solution
  2. concentrationThe mixture is then concentrated under reduced pressure at a temperature of approximately 40° C
  3. additionWater (200 ml) and dichloromethane (300 ml) are added to the residue
  4. extractionAfter decantation and extractions
  5. washthe combined organic phases are washed with salt water
  6. dry with materialdried over Na2SO4
  7. concentrationthen concentrated under reduced pressure at 40° C
  8. customThe solid obtained
  9. washis washed with petroleum ether
  10. customdried (4.4 g; 87% yield)

Sources & evidence

ORD record
ord-9ce81bb4aa734f1a91760dbecdba343c
Source dataset
uspto-grants-2009_03
Patent number
US07501525B2

Reaction notes

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