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

HRID 601032Notes

Reaction equation

HRID 601032 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-86fe6a3a92ec425d8b5f686d0b34f3d5
Source dataset
uspto-grants-2011_03
Patent number
US07902239B2

Reaction notes

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