Allyl bromide → 2-(Allyloxy)-5-bromo-1-fluoro-3-nitrobenzene

HRID 1373762Notes

Reaction equation

HRID 1373762 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([OH:9])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[CH2:13](Br)[CH:14]=[CH2:15].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:15]([O:9][C:5]1[C:4]([N+:10]([O-:12])=[O:11])=[CH:3][C:2]([Br:1])=[CH:7][C:6]=1[F:8])[CH:14]=[CH2:13]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 6881164-Bromo-2-fluoro-6-nitrophenol

Product 1

HCID 210753692-(Allyloxy)-5-bromo-1-fluoro-3-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 4-bromo-6-fluoro-2-nitrophenol (2 g, 8.49 mmol), allyl bromide (0.88 mL, 10.07 mmol) and K2CO3 (2.34 g, 16.98 mmol) in DMF (20 mL) was stirred at 45° C. overnight. Inorganic salts were filtered off, and the filtrate was concentrated to provide the crude product, which was directly used for next step without further purification. MS (DCI/NH3) m/z 245.92 (M+H)+; 1H NMR (400 MHz, DMSO-D6) δ ppm 4.70 (d, J=6.14 Hz, 2 H) 5.27 (d, J=10.43 Hz, 1 H) 5.37 (dd, J=17.18, 1.53 Hz, 1 H) 5.92–6.02 (m, 1 H) 8.03–8.06 (m, 2 H).

Workup

  1. filtrationInorganic salts were filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-02d71e6ab5174db4bf768abfbba017e6
Source dataset
uspto-grants-2007_01
Patent number
US07163939B2

Reaction notes

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