Nitrogen → Methyl 2,6-Difluoro-3-nitrobenzoate

HRID 1943842Notes

Reaction equation

HRID 1943842 reaction equation
[F:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]([F:14])[C:3]=1[C:4]([OH:6])=[O:5].[N+](=[CH2:17])=[N-].[Si](C=[N+]=[N-])(C)(C)C.N#N>CO>[F:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]([F:14])[C:3]=1[C:4]([O:6][CH3:17])=[O:5]

Participants

6

Reactant 4

HCID 947NitrogenHCID 9550DiazomethaneHCID 167693TrimethylsilyldiazomethaneHCID 3026292,6-Difluoro-3-nitrobenzoic acid

Product 1

HCID 43449035Methyl 2,6-Difluoro-3-nitrobenzoateYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 1 L flask was charged with 2,6-difluoro-3-nitrobenzoic acid (17.0 g, 83.7 mmol) and MeOH (170 mL, 0.5M). The flask was placed in a cold water bath, and an addition funnel charged with a 2M solution of trimethylsilyl (“TMS”) diazomethane in hexanes (209 mL, 419 mmol) was attached to the flask. The TMS diazomethane solution was added slowly to the reaction flask over the course of 2 hours. A large excess of reagent was required in order for the reaction to reach completion as determined by the ceased evolution of N2 upon further addition of reagent. The volatiles were removed in vacuo to afford methyl 2,6-difluoro-3-nitrobenzoate as a solid (18.2 g, 99%). The material was taken directly onto Step B.

Workup

  1. customThe flask was placed in a cold water bath, and an addition funnel
  2. customA large excess of reagent was required in order for the reaction
  3. customThe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-bc5c627d0e9745918ced989c78eae011
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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