2-Chloroethanol → 2-(2-Chloroethoxy)-4-fluoro-1-nitrobenzene

HRID 2240055Notes

Reaction equation

HRID 2240055 reaction equation
[Cl:1][CH2:2][CH2:3][OH:4].[Li+].CC([N-]C(C)C)C.F[C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[N+:21]([O-:23])=[O:22]>C1COCC1.O>[Cl:1][CH2:2][CH2:3][O:4][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[N+:21]([O-:23])=[O:22]

Participants

6

Reactant 3

HCID 342-ChloroethanolHCID 679672,4-DifluoronitrobenzeneHCID 2724682Lithium diisopropylamide

Product 1

HCID 431355982-(2-Chloroethoxy)-4-fluoro-1-nitrobenzeneYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In a round bottom flask under nitrogen, 2-chloro-ethanol (8.3 mL, 120 mmoles) in THF (40 mL) was cooled to 0° C. LDA (60 mL, 120 mmoles) was added dropwise, while maintaining the temperature constant at 0° C. The mixture was stirred at this temperature for 15 minutes, followed by the addition of 2,4-difluoronitrobenzene (11 mL, 100 mmoles). The mixture was stirred at room temperature overnight. Reaction mixture was diluted with water, extracted with EtOAc, washed with brine (1×), dried over Na2SO4, and concentrated under vacuum, to afford the title compound as an off-white solid (20.0 g, 91 mmoles).

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. customReaction mixture
  3. extractionextracted with EtOAc
  4. washwashed with brine (1×)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-973d58b164e845c19d5a660df2176263
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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