1,2-Dibromoethane → HCID 24688592, compound

HRID 2108361Notes

Reaction equation

HRID 2108361 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([OH:8])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[Br:18][CH2:19][CH2:20]Br>C(#N)C>[Br:18][CH2:19][CH2:20][O:8][C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 99375-Fluoro-2-nitrophenolHCID 11430Potassium Carbonate

Product 1

HCID 24688592HCID 24688592, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 5-fluoro-2-nitrophenol (1.5 g, 9.55 mmole) in acetonitrile (100 mL) under a nitrogen atmosphere was treated with potassium carbonate (4.5 g, 32.6 mmole) and 1,2-dibromoethane (16.0 mL, 186 mmole), The reaction mixture was heated to 70° C. for 40 hours. The reaction was then filtered and concentrated. The crude material was purified by flash chromatography (SiO2, 20% ethyl acetate/hexane) to give 2-(2-bromoethoxy)-4-fluoro-1-nitrobenzene (2.5 g, 98%). 1HNMR (CDCl3) δ 7.97 (m, 1H), 6.79 (m, 2H), 4.40 (t, 2H, J=8.0 Hz), 3.69 (t, 2H, J =8.0 Hz).

Workup

  1. filtrationThe reaction was then filtered
  2. concentrationconcentrated
  3. customThe crude material was purified by flash chromatography (SiO2, 20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f3f9f77cf757446fa462e6f890797de5
Source dataset
uspto-grants-2009_04
Patent number
US07514435B2

Reaction notes

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