Water → 1-Bromo-2-fluoro-3-methoxy-4-nitrobenzene

HRID 1880972Notes

Reaction equation

HRID 1880972 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([O:9][CH3:10])[C:3]=1[F:11].B1([O-])OO1.[OH2:16].[OH2:17].O.O.[Na+].O>C(O)(C(F)(F)F)=O.C(O)(=O)C>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([N+:6]([O-:17])=[O:16])=[C:4]([O:9][CH3:10])[C:3]=1[F:11]

Participants

6

Reactant 3

HCID 962WaterHCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrateHCID 579555294-Bromo-3-fluoro-2-methoxyaniline

Product 1

HCID 579555891-Bromo-2-fluoro-3-methoxy-4-nitrobenzeneYield 40%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
60 °C

Procedure

To 4-bromo-3-fluoro-2-methoxyaniline (1 g, 4.5 mmol) in a mixture of TFA and acetic acid (10 mL/10 mL) was added sodium perborate tetrahydrate (3.2 g, 21 mmol). The reaction mixture was warmed up to 60° C. and heated for 24 h. It was then diluted to water, extracted with ethyl acetate. The product was obtained by flash column as a yellow solid (450 mg, 40%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 4.11 (s, 3 H) 7.40 (dd, J=9.0, 6.2 Hz, 1 H) 7.54 (dd, J=9.0, 1.9 Hz, 1 H).

Workup

  1. temperatureheated for 24 h
  2. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-f708c29686704fed8787968856a63b7b
Source dataset
uspto-grants-2012_11
Patent number
US08318727B2

Reaction notes

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