Chlorodifluoromethane → 1-(Difluoromethoxy)-2-nitrobenzene

HRID 2294105Notes

Reaction equation

HRID 2294105 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([O-:3])=[O:2].[OH-].[Na+].Cl[CH:14]([F:16])[F:15]>O1CCOCC1.O>[F:15][CH:14]([F:16])[O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 6372ChlorodifluoromethaneHCID 69472-NitrophenolHCID 14798Sodium Hydroxide

Product 1

HCID 27370111-(Difluoromethoxy)-2-nitrobenzene

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2-nitrophenol (6.01 g, 43.2 mmol) and sodium hydroxide (8.6 g, 216 mmol) in 50 mL of dioxane and 50 mL of water was heated to 70° C. and chlorodifluoromethane gas was introduced. The mixture was diluted with water and extracted with diethyl ether. The organic phase was washed with aqueous sodium hydroxide and then brine, dried (MgSO4) and concentrated to give 1-difluoromethoxy-2-nitrobenzene (8.21 g, 43.4 mmol) as an oil.

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic phase was washed with aqueous sodium hydroxide
  3. dry with materialbrine, dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-45a75c1220df430e9f80d7bb95f713f4
Source dataset
uspto-grants-1997_11
Patent number
US05688795

Reaction notes

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