Trimethylsilyldiazomethane → Methyl 4-amino-2-fluoro-5-methoxybenzoate

HRID 914186Notes

Reaction equation

HRID 914186 reaction equation
[NH2:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:13])[CH:3]=1.[Si](C=[N+]=[N-])(C)(C)[CH3:15]>C(Cl)Cl.CO>[NH2:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:5]([C:6]([O:8][CH3:15])=[O:7])=[C:4]([F:13])[CH:3]=1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 529829634-Amino-2-fluoro-5-methoxybenzoic acid

Product 1

HCID 57955533Methyl 4-amino-2-fluoro-5-methoxybenzoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To an amount of 4-amino-2-fluoro-5-methoxybenzoic acid (4 g, 21.62 mmole) that was dissolved in DCM (40 ml) and MeOH (11 mL), was added TMS-diazomethane (16.2 mL, 32.43 mmole) slowly. The mixture was stirred at r.t for 30 mins. After the removal of solvent, the resulting tan solid (4.0 g, 93%) carried onto the next reaction without any purification. [M+H] calc'd for C9H10FNO3, 200. found 200.

Workup

  1. customAfter the removal of solvent
  2. customthe resulting tan solid (4.0 g, 93%) carried onto the next reaction without any purification

Sources & evidence

ORD record
ord-61ab0034231d451ba42ffcfbf4801296
Source dataset
uspto-grants-2011_09
Patent number
US08026234B2

Reaction notes

Loading…