Isopropanol → 4-Bromo-2-isopropoxy-1-nitro-benzene

HRID 518793Notes

Reaction equation

HRID 518793 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH:18]([OH:21])([CH3:20])[CH3:19]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:21][CH:18]([CH3:20])[CH3:19])[CH:3]=1

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 10796Cesium carbonateHCID 27833624-Bromo-2-fluoro-1-nitrobenzene

Product 1

HCID 226243214-Bromo-2-isopropoxy-1-nitro-benzene

Conditions

Temperature
85 °C

Procedure

A mixture of 10.0 g of 4-bromo-2-fluoro-1-nitrobenzene, 44.4 g of caesium carbonate and 100 ml of isopropanol is heated at 85° C. (bath) for 1 h 30, and then left to cool to ambient temperature. The mixture is concentrated under vacuum and the residue is taken up with 400 ml of water and 300 ml of ethyl acetate. The aqueous phase is extracted with 100 ml of ethyl acetate and the combined organic phases are washed twice with 200 ml of water. The organic phases are dried over magnesium sulfate and concentrated under vacuum, so as to obtain 11.59 g of crude 4-bromo-1-nitro-2-(propan-2-yloxy)benzene in the form of a yellow oil which crystallizes. TLC: Rf=0.52 (dichloromethane/heptane (1/1)).

Workup

  1. waitleft
  2. temperatureto cool to ambient temperature
  3. concentrationThe mixture is concentrated under vacuum
  4. extractionThe aqueous phase is extracted with 100 ml of ethyl acetate
  5. washthe combined organic phases are washed twice with 200 ml of water
  6. dry with materialThe organic phases are dried over magnesium sulfate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a9bcc0f40d234a85aa015ef4921e2c87
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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