Ethyl Acetate → HCID 57435883, compound

HRID 30573Notes

Reaction equation

HRID 30573 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH2:9][CH:10]([F:13])[CH2:11]I)[CH:3]=1.C1CCN2C(=NCCC2)CC1.CCOC(C)=O>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH2:9][C:10]([F:13])=[CH2:11])[CH:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 57435882HCID 57435882, compound

Product 1

HCID 57435883HCID 57435883, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.405 gm (1.1 mmol) of 1-bromo-3-(3-fluoro-4-iodobutyl)-benzene in CH2Cl2 was treated with 0.82 mL (5.5 mmol) of DBU at room temperature, stirred at room temperature for 24 h and poured into EtOAc. The resultant organic phase was washed sequentially with water and brine, dried over Na2SO4 and concentrated under reduced pressure. Chromatography of the concentrate on silica gel with a gradient of hexanes to 7.0% EtOAc-hexanes gave 1-bromo-3-(3-fluorobut-3-enyl)benzene as an oil, 0.20 gm (80% yield); 1H NMR (400 MHz, CDCl3) δ: 2.45 (m, 2H), 2.78 (t, 2H, J=7.8 Hz), 3.29 (dd, 1H, J=2.8, 50.1 Hz), 4.50 (dd, 1H, J=2.8, 7.3 Hz), 7.12 (m, 2H), 7.32 (m, 2H).

Workup

  1. washThe resultant organic phase was washed sequentially with water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. concentrationChromatography of the concentrate on silica gel with a gradient of hexanes to 7.0% EtOAc-hexanes

Sources & evidence

ORD record
ord-ffd7300ceac44164abba5b7f798ea013
Source dataset
uspto-grants-2008_09
Patent number
US07423158B2

Reaction notes

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