1-Bromo-2-Chloroethane → HCID 22326897, compound

HRID 1179239Notes

Reaction equation

HRID 1179239 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[OH:12].Br[CH2:14][CH2:15][Cl:16].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:16][CH2:15][CH2:14][O:12][C:4]1[CH:5]=[CH:6][C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 767382-Methoxy-4-nitrophenol

Product 1

HCID 22326897HCID 22326897, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-methoxy-4-nitro-phenol (2.50 g, 14.8 mmol), 1-bromo-2-chloro-ethane (1.35 mL, 16.3 mmol) and potassium carbonate (4.08 g, 29.6 mmol) in DMF (50 mL) in a sealed tube was heated at 90° C. for 18 h. The reaction was cooled and filtered, washing with ethyl acetate. The filtrate was washed with sodium bicarbonate, water (4 times) and brine, was dried (sodium sulfate) and evaporated. Purification by flash chromatography (SiO2) eluted with 35:65 ethyl acetate:hexanes provided 1-(2-chloro-ethoxy)-2-methoxy-4-nitro-benzene (1.93 g, 56% yield) as an off-white solid. 1H-NMR (DMSO-d6, 500 MHz) 7.89 (dd, 1H), 7.76 (d, 1H), 7.21 (d, 1H), 4.41 (t, 2H), 4.00 (t, 2H), 3.90 (s, 3H) ppm; HPLC (Method A) 3.781 min.

Workup

  1. temperatureThe reaction was cooled
  2. filtrationfiltered
  3. washwashing with ethyl acetate
  4. washThe filtrate was washed with sodium bicarbonate, water (4 times) and brine
  5. dry with materialwas dried (sodium sulfate)
  6. customevaporated
  7. customPurification by flash chromatography (SiO2)
  8. washeluted with 35:65 ethyl acetate

Sources & evidence

ORD record
ord-4c354cb50ad748608a6bab6e2739fac5
Source dataset
uspto-grants-2007_10
Patent number
US07279469B2

Reaction notes

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