4-Nitrophenol → 4-Nitrophenyl 2-bromo-2-methylpropanoate

HRID 1867779Notes

Reaction equation

HRID 1867779 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.[Br:18][C:19]([CH3:24])([CH3:23])[C:20](Br)=[O:21]>O1CCCC1>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:20](=[O:21])[C:19]([Br:18])([CH3:24])[CH3:23])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 8471TriethylamineHCID 886852-Bromo-2-methylpropionyl bromide

Product 1

HCID 142318974-Nitrophenyl 2-bromo-2-methylpropanoateYield 85.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-Nitrophenol (8 gm, 56 mmol) in 100 ml anhydrous tetrahydrofuran was placed under a nitrogen atmosphere and cooled in an icebath. To this was added triethylamine (6.2 g, 61 mmol) followed by the dropwise addition of bromoisobutyryl bromide (14.1 g, 61 mmol) in 20 ml anhydrous tetrahydrofuran over 5 min. After stirring for 16 h, the solids were filtered off and the solution concentrated, and then recrystallized from 100 ml methanol to give 13.8 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-93eb0c417ac942a6a9a3f2126e9f7437
Source dataset
uspto-grants-2009_12
Patent number
US07632875B2

Reaction notes

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