Methanol → Methyl 2-fluoro-5-methoxy-4-nitrobenzoate

HRID 1687820Notes

Reaction equation

HRID 1687820 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8]([O:14][CH3:15])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:16]1(C)C=CC=CC=1.CO.C[Si](C=[N+]=[N-])(C)C>CCOCC>[CH3:16][O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([O:14][CH3:15])[C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:2]=1[F:1]

Participants

6

Reactant 4

HCID 887MethanolHCID 1140TolueneHCID 167693TrimethylsilyldiazomethaneHCID 579556142-Fluoro-5-methoxy-4-nitrobenzoic acid

Product 1

HCID 67076410Methyl 2-fluoro-5-methoxy-4-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Into a round bottom flask, 2-fluoro-5-methoxy-4-nitro-benzoic acid (2.84 g, 0.0132 mol;), toluene (25 mL, 0.23 mol), methanol (5 mL, 0.1 mol;) were added. 2.00 M of trimethylsilyldiazomethane in ether (7.92 mL) was added drop wise at 5° C. The reaction was stirred at room temperature for 2 hours. The solvent was removed under vacuum to afford a yellow solid. The solid was triturated with 10% Et2O and hexane to give 2-fluoro-5-methoxy-4-nitro-benzoic acid methyl ester as an off white solid (2.84, 93%). 1H-NMR (DMSO-D6, 400 MHz): δ 8.06 (d, 1H), 7.70 (d, 1H). 4.14 (s, 3H), 3.91 (s, 3H).

Workup

  1. customThe solvent was removed under vacuum
  2. customto afford a yellow solid
  3. customThe solid was triturated with 10% Et2O and hexane

Sources & evidence

ORD record
ord-cad7276ddfc5414d89b76e2c238c232d
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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