4-Fluoro-3-nitroaniline → Tert-butyl 4-fluoro-3-nitrophenylcarbamate

HRID 467547Notes

Reaction equation

HRID 467547 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[C:12]([O:16][C:17](=O)[O:18]C(C)(C)C)([CH3:15])([CH3:14])[CH3:13]>C(O)C>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:17](=[O:18])[O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 677684-Fluoro-3-nitroanilineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 11118665Tert-butyl 4-fluoro-3-nitrophenylcarbamateYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-fluoro-3-nitroaniline (30 g, 0.192 mol), di-t-butylcarbonate (84 g, 0.384 mol) was stirred in ethanol (300 mL) at r.t. for 1 week. The solvents were removed in vacuo and chromatographic purification (ethyl acetate-hexane) of the residue gave tert-butyl 4-fluoro-3-nitrophenylcarbamate (43 g, 88%) as a white solid.

Workup

  1. customThe solvents were removed in vacuo and chromatographic purification (ethyl acetate-hexane) of the residue

Sources & evidence

ORD record
ord-2b71530c32fc49d6a1ad2b00fc401a52
Source dataset
uspto-grants-2014_01
Patent number
US08623857B2

Reaction notes

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