Potassium Hydroxide → (2-Bromo-6-nitrophenyl)methanol

HRID 459796Notes

Reaction equation

HRID 459796 reaction equation
[Br:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:3]=1[CH2:4][O:5]C(=O)C.[OH-].[K+]>O>[Br:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:3]=1[CH2:4][OH:5]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 588241222-Bromo-6-nitrobenzyl Acetate

Product 1

HCID 18444469(2-Bromo-6-nitrophenyl)methanolYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of acetic acid 2-bromo-6-nitro-benzyl ester (536 mg, 1.96 mmol) in water (20 ml) was added KOH solution (10%, 1.5 ml). The reaction was heated under reflux overnight. After cooling to room temperature, the reaction mixture was extracted with ethyl acetate. The combined extracts were treated with MgSO4, and concentrated under vacuum to give (2-bromo-6-nitro-phenyl)-methanol (389 mg, 86%) as a yellow solid. 1H NMR (CDCl3, 300 MHz) δ: 4.93 (d, J=7.43 Hz), 7.354 (t, J=8.10 Hz), 7.84 (dd, J=1.23 Hz, 8.17 Hz), 7.89(dd, J=1.22 Hz, 8.03 Hz).

Workup

  1. temperatureThe reaction was heated
  2. temperatureunder reflux overnight
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. additionThe combined extracts were treated with MgSO4
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-d85cb514e8824ed4910b44147713e467
Source dataset
uspto-grants-2007_03
Patent number
US07196087B2

Reaction notes

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