Ethanol → 2-Ethoxy-5-nitro-1,3-bis(trifluoromethyl)benzene

HRID 62719Notes

Reaction equation

HRID 62719 reaction equation
[CH2:1]([OH:3])[CH3:2].[OH-].[K+].Cl[C:7]1[C:12]([C:13]([F:16])([F:15])[F:14])=[CH:11][C:10]([N+:17]([O-:19])=[O:18])=[CH:9][C:8]=1[C:20]([F:23])([F:22])[F:21]>CS(C)=O>[CH2:1]([O:3][C:7]1[C:8]([C:20]([F:21])([F:22])[F:23])=[CH:9][C:10]([N+:17]([O-:19])=[O:18])=[CH:11][C:12]=1[C:13]([F:14])([F:15])[F:16])[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 113008542-Chloro-5-nitro-1,3-bis(trifluoromethyl)benzene

Product 1

HCID 866665952-Ethoxy-5-nitro-1,3-bis(trifluoromethyl)benzeneYield 96.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Ethanol (20 mL, 343 mmol) was treated with potassium hydroxide (956 mg, 17.0 mmol) and the mixture was stirred at RT for 1 h. A solution of 2-chloro-5-nitro-1,3-bis(trifluoromethyl)benzene (1) (1.00 g, 3.41 mmol) in DMSO (10 mL) was added dropwise. The resultant mixture was stirred at RT for 1 h. The mixture was partitioned between EtOAc and water and the aqueous phase was extracted twice with EtOAc. The combined organic phases were washed with brine, dried over MgSO4, filtered and the solvent removed in vacuo to afford 2-ethoxy-5-nitro-1,3-bis(trifluoromethyl)benzene (2) (1.00 g, 93%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ: 8.72 (2H, s), 4.21 (2H, q), 1.41 (3H, t).

Workup

  1. customThe mixture was partitioned between EtOAc and water
  2. extractionthe aqueous phase was extracted twice with EtOAc
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-74e0c5cb1e9943aa826529780e22bf7a
Source dataset
uspto-grants-2016_09
Patent number
US09447028B2

Reaction notes

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