Methanol → Methyl 2-fluoro-6-nitrobenzoate

HRID 1686994Notes

Reaction equation

HRID 1686994 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:3]=1[C:4]([OH:6])=[O:5].CO.[N+](=[CH2:18])=[N-]>C1COCC1>[CH3:18][O:5][C:4](=[O:6])[C:3]1[C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=[CH:10][C:2]=1[F:1]

Participants

5

Reactant 3

HCID 887MethanolHCID 9550DiazomethaneHCID 6037582-Fluoro-6-nitrobenzoic acid

Product 1

HCID 597752Methyl 2-fluoro-6-nitrobenzoateYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-fluoro-6-nitro-benzoic acid (2.15 g, 0.0116 mol) in THF (25 mL)/methanol (10 mL) under nitrogen was added diazomethane (5.8 mL) dropwise. The reaction mixture was stirred at room temperature overnight. HPLC indicated complete conversion to product. The reaction solvent was removed in vacuo to give a tannish yellow solid 2-Fluoro-6-nitro-benzoic acid methyl ester (2.2 g, 96% yield). 1H NMR (400 MHz, DMSO-d6) δ 8.12 (d, 1H, J=7.6 Hz), 7.88 (m, 2H), 3.92 (s, 3H).

Workup

  1. customThe reaction solvent was removed in vacuo

Sources & evidence

ORD record
ord-4dc8d20f70b1449eb7ab69b1e3a164d5
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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