1,2-Dibromoethane → 1-(2-Bromoethoxy)2-methoxy-4-nitrobenzene

HRID 1181355Notes

Reaction equation

HRID 1181355 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:12])[C:7]([O:10][CH3:11])=[CH:8][CH:9]=1)([O-:3])=[O:2].[C:13](=O)([O-])[O-].[Cs+].[Cs+].[Br:19][CH2:20]CBr>CN(C=O)C.CCOC(C)=O>[Br:19][CH2:20][CH2:11][O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=1[O:12][CH3:13]

Participants

6

Reactant 3

HCID 78391,2-DibromoethaneHCID 10796Cesium carbonateHCID 694712-Methoxy-5-nitrophenol

Product 1

HCID 129372541-(2-Bromoethoxy)2-methoxy-4-nitrobenzeneYield 42.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

4-Nitroguaiacol (1.0171 g, 6.0134 mmol) was dissolved in anhydrous DMF (20 mL). Cesium carbonate (3.9207 g, 12.0268 mmol) and 1,2-dibromoethane (2.07 mL, 24.0534 mmol) were added. The reaction was heated to 80° C. and stirred for 18 h. The mix was then cooled to RT and diluted with EtOAc (100 mL), washed with water (3×100 mL), and the organics dried over MgSO4, filtered and concentrated. The residue was filtered through a 3″ plug of basic alumina (100% CH2Cl2) to give 0.7075 g (2.5634 mmol, 42%) of the product as a white solid. 1H NMR (CDCl3) δ 7.90 (d, 1H, J=8.8 Hz), 7.78 (s, 1H), 6.92 (d, 1H, J=8.8 Hz), 4.42 (t, 2H, J=6.4 Hz), 3.96 (s, 3H), 3.70 (t, 2H, J=6.5 Hz).

Workup

  1. temperatureThe mix was then cooled to RT
  2. washwashed with water (3×100 mL)
  3. dry with materialthe organics dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. filtrationThe residue was filtered through a 3″ plug of basic alumina (100% CH2Cl2)

Sources & evidence

ORD record
ord-aaa5a19a14f447919e5d173dd360c452
Source dataset
uspto-grants-2007_10
Patent number
US07285557B2

Reaction notes

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