2-Chloroethanol → HCID 69296428, compound

HRID 2219008Notes

Reaction equation

HRID 2219008 reaction equation
[Cl:1][CH2:2][CH2:3][OH:4].C([N-]C(C)C)(C)C.[Li+].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:15]1([N+:21]([O-:23])=[O:22])[CH:16]=[CH:17][C:18]([F:20])=[CH:19][CH2:14]1

Participants

6

Reactant 3

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

Product 1

HCID 69296428HCID 69296428, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-chloro-ethanol (1) (8.3 ml, 120 mmoles) in THF, under nitrogen, was cooled to 0° C., treated dropwise with lithium diisopropylamide (LDA) (60 ml, 120 mmoles, while maintaining the temperature constant at 0° C. The mixture was stirred at 0° C. for 15 minutes, treated with 2,4-difluoro-1-nitro-benzene (1) (11 ml, 100 mmoles), stirred at room temperature overnight, diluted with water and extracted with EtOAc. The extracts were combined, washed with brine, dried over Na2SO4, and concentrated under vacuum to afford the title compound as an off-white solid (20.0 g, 91 mmoles), identified by HNMR and mass spectral analyses.

Workup

  1. stirringstirred at room temperature overnight
  2. extractionextracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-5d71950243974b3280be0538074d184f
Source dataset
uspto-grants-2008_08
Patent number
US07414051B2

Reaction notes

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