2,4-Dinitrophenol → HCID 57980218, compound

HRID 1867778Notes

Reaction equation

HRID 1867778 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[OH:13])([O-:3])=[O:2].C(N(CC)CC)C.[Br:21][C:22]([CH3:27])([CH3:26])[C:23](Br)=[O:24]>O1CCCC1>[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[O:13][C:23](=[O:24])[C:22]([Br:21])([CH3:27])[CH3:26])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 14932,4-DinitrophenolHCID 8471TriethylamineHCID 886852-Bromo-2-methylpropionyl bromide

Product 1

HCID 57980218HCID 57980218, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2,4-Dinitrophenol (9.6 gm, 52 mmol) in 80 ml anhydrous tetrahydrofuran was placed under a nitrogen atmosphere and cooled in an icebath. To this was added triethylamine (5.80 g, 57 mmol) followed by the dropwise addition of bromoisobutyryl bromide (15.6 g, 67 mmol) in 20 ml anhydrous tetrahydrofuran over 5 min. After stirring for 4 h, the solids were filtered off and the solution concentrated, and then recrystallized from 100 ml methanol to give 15.8 g yellow solid, >99% pure by HPLC.

Workup

  1. temperaturecooled in an icebath
  2. filtrationthe solids were filtered off
  3. concentrationthe solution concentrated
  4. customrecrystallized from 100 ml methanol

Sources & evidence

ORD record
ord-2bdbd15a1c5d4cc098b65f1eb12794a7
Source dataset
uspto-grants-2009_12
Patent number
US07632875B2

Reaction notes

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