Nitric Acid → 4-(Difluoromethoxy)-2-nitrophenol

HRID 1968981Notes

Reaction equation

HRID 1968981 reaction equation
[F:1][CH:2]([F:11])[O:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[N+:12]([O-])([OH:14])=[O:13]>ClCCCl>[F:1][CH:2]([F:11])[O:3][C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[C:8]([N+:12]([O-:14])=[O:13])[CH:9]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 27741244-(Difluoromethoxy)phenol

Product 1

HCID 594440714-(Difluoromethoxy)-2-nitrophenolYield 85.9%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

4-(Difluoromethoxy)phenol (500 mg, 3.12 mmol) was dissolved in DCE (3 mL). The reaction mixture was cooled to 0° C. and nitric acid (0.488 mL, 10.92 mmol) was added dropwise over 10 min. The reaction mixture was stirred for a further hour at 0° C., then poured into an ice/water mix (5 g in 5 mL). DCE (10 mL) was added and the layers separated. The organic layer was dried (MgSO4) and evaporated to dryness to give a crude brown oil (550 mg). Material was carried forward without further purification, as no separation between products was found in TLC solvent systems used. (M−H)−=204.

Workup

  1. additionmix (5 g in 5 mL)
  2. customthe layers separated
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-7292f49dd4bc418fab12a0903b1a163a
Source dataset
uspto-grants-2013_04
Patent number
US08426443B2

Reaction notes

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