2-Methoxyethanol → HCID 57500710, compound

HRID 1811561Notes

Reaction equation

HRID 1811561 reaction equation
[F:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[CH:4][C:3]=1[NH2:9].[CH3:10][O:11][CH2:12][CH2:13][OH:14].C(=O)([O-])[O-].[Cs+].[Cs+]>[Cu]I>[F:1][C:2]1[CH:7]=[C:6]([O:14][CH2:13][CH2:12][O:11][CH3:10])[CH:5]=[CH:4][C:3]=1[NH2:9]

Participants

5

Reactant 3

HCID 80192-MethoxyethanolHCID 10796Cesium carbonateHCID 1856942-Fluoro-4-iodoaniline

Product 1

HCID 57500710HCID 57500710, compoundYield 41.1%

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Conditions

Temperature
110 °C

Procedure

A mixture of 2-fluoro-4-iodo-phenylamine (2.3672 g, 10 mmol), 2-methoxyethanol (13 ml, 164 mmol), copper(I)iodide (190 mg, 1 mmol), 1,10-phenanthridine (360 mg, 2 mmol), and cesium carbonate (4.55 g mg, 14 mmol) was sealed and heated at 110° C. After 17 hours, the crude mixture was extracted with CH2Cl2 and brine. Organic phase was dried over MgSO4, filtered, and concentrated. The residue was purified by column chromatography on silica gel with hexane/ethyl acetate (1:1 v/v) twice to give 2-fluoro-4-(2-methoxy-ethoxy)-phenylamine as an oil (761 mg, 41%). Exact mass calculated for C9H12FNO2 185.09. found 186.0 (MH+).

Workup

  1. customwas sealed
  2. extractionthe crude mixture was extracted with CH2Cl2 and brine
  3. dry with materialOrganic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel with hexane/ethyl acetate (1:1 v/v) twice

Sources & evidence

ORD record
ord-3c13edd876b24c0dba85dfac78c4b2d2
Source dataset
uspto-grants-2013_01
Patent number
US08362248B2

Reaction notes

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