Isopropanol → 1-Chloro-5-isopropoxy-2-methyl-4-nitrobenzene

HRID 1850897Notes

Reaction equation

HRID 1850897 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](F)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[CH3:12].C([O-])([O-])=O.[Cs+].[Cs+].[CH3:19][CH:20]([OH:22])[CH3:21]>>[Cl:1][C:2]1[CH:7]=[C:6]([O:22][CH:20]([CH3:21])[CH3:19])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[CH3:12]

Participants

4

Reactant 3

HCID 3776Isopropanol2×HCID 10796Cesium carbonateHCID 101039792-Chloro-4-fluoro-5-nitrotoluene

Product 1

HCID 457903241-Chloro-5-isopropoxy-2-methyl-4-nitrobenzene

Procedure

To a solution of 25 g (0.131 mol) of 2-chloro-4-fluoro-5-nitrotoluene in 250 ml of 2-propanol is added 208 g (0.659 mol, 5 eq.) of Cs2CO3. The mixture is stirred at 60° C. overnight and most of the 2-propanol is evaporated under reduced pressure. Water is added and the solution is extracted with EtOAc. The organic layers are combined, dried over MgSO4, concentrated and the crude product filtrated over a silica plug (eluent: 95/5 hexanes/EtOAc) to afford 2-chloro-4-isopropoxy-5-nitrotoluene as a pale yellow fluffy solid.

Workup

  1. customis evaporated under reduced pressure
  2. additionWater is added
  3. extractionthe solution is extracted with EtOAc
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. filtrationthe crude product filtrated over a silica plug (eluent: 95/5 hexanes/EtOAc)

Sources & evidence

ORD record
ord-6bcaaf0ce455430998a558634ebb0886
Source dataset
uspto-grants-2015_02
Patent number
US08957081B2

Reaction notes

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