2-Methoxyethanol → HCID 53255561, compound

HRID 1041748Notes

Reaction equation

HRID 1041748 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N+:9]([O-:11])=[O:10].[CH3:12][O:13][CH2:14][CH2:15][OH:16]>CN(C=O)C>[F:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([O:16][CH2:15][CH2:14][O:13][CH3:12])[C:3]=1[N+:9]([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 80192-MethoxyethanolHCID 879221,3-Difluoro-2-nitrobenzene

Product 1

HCID 53255561HCID 53255561, compoundYield 49.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1,3-difluoro-2-nitro-benzene (1.0 g), 2-methoxyethanol (480 mg), and CsCO3 (3.6 g) in DMF (20 mL) was heated at 60° C. for 16 hours. The reaction mixture was filtered, concentrated, and purified by silica gel chromatography to afford 675 mg of 1-fluoro-3-(2-methoxy-ethoxy)-2-nitro-benzene: 1H NMR (300 MHz, CDCl3) δ 7.4 (dd, 1H), 6.8 (m, 2H), 4.2 (t, 2H), 3.7 (t, 2H), 3.4 (s, 3H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-c93940c5813240918c29d87887a9865e
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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