1,3-Dibromopropane → 2-(3-Bromopropoxy)-1-methoxy-4-nitrobenzene

HRID 1057988Notes

Reaction equation

HRID 1057988 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[OH:12].C(=O)([O-])[O-].[K+].[K+].[Br:19][CH2:20][CH2:21][CH2:22]Br>CN(C)C=O.ClCCl>[Br:19][CH2:20][CH2:21][CH2:22][O:12][C:4]1[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Participants

6

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 694712-Methoxy-5-nitrophenol

Product 1

HCID 186726462-(3-Bromopropoxy)-1-methoxy-4-nitrobenzene

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

A stirred mixture of 2-methoxy-5-nitrophenol (5.0 g. 29.6 mmol) and powdered potassium carbonate (6.5 g, 47.4 mmol) in dimethylformamide (50 mL) was treated with 1,3-dibromopropane (80.8 g, 0.4 mol), heated to 90° C. for 2 h, cooled, diluted with dichloromethane (250 mL), and filtered. The filtrate was concentrated in vacuo and the residue was crystallized from methanol. The resulting solid was triturated with 30% ethyl acetate/hexane and then with boiling 30% ethyl acetate/hexane. The combined organic phases were concentrated in vacuo to give the title compound: 1H NMR (300 MHz, CDCl3) δ7.92 (dd, 1H), 7.75 (d, 1H), 6.92 (dd, 1H), 4.20 (t, 2H), 3.95 (s, 3H), 3.62 (t, 2H), 2.40 (m, 2H).

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was crystallized from methanol
  5. customThe resulting solid was triturated with 30% ethyl acetate/hexane
  6. concentrationThe combined organic phases were concentrated in vacuo

Sources & evidence

ORD record
ord-0c9b52799a784be0bfb5b459fa1cf985
Source dataset
uspto-grants-2003_02
Patent number
US06515027B1

Reaction notes

Loading…