Methanol → Methyl 2-fluoro-6-nitrobenzoate

HRID 1040685Notes

Reaction equation

HRID 1040685 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-a4734583ab8f40ae9ae6dcbf83f245f8
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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