1,3-Butadiene → HCID 68770669, compound

HRID 1172322Notes

Reaction equation

HRID 1172322 reaction equation
[CH2:1]=[CH:2][CH:3]=[CH2:4].[Cl:5][C:6]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:7]=1[CH:8]=[CH:9][N+:10]([O-:12])=[O:11]>C1(C)C=CC=CC=1>[Cl:5][C:6]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:7]=1[C@H:8]1[C@H:9]([N+:10]([O-:12])=[O:11])[CH2:4][CH:3]=[CH:2][CH2:1]1

Participants

4

Reactant 2

HCID 78451,3-ButadieneHCID 68769313HCID 68769313, compound

Product 1

HCID 68770669HCID 68770669, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A 10 mL solution of 1:1 1,3-butadiene in toluene stored at −20° C. and 2-chloro-4-fluoro-β-nitrostyrene (2.0 g, 10 mmol) were added to a pressure tube and sealed. The solution was heated to 110° C. and stirred for three days. The reaction mixture was cooled to room temperature, concentrated and the residue was crystallized from hexanes to give the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.23-7.28 (m, 1H), 7.11-7.25 (m, 3H), 6.94-7.01 (m, 1H), 5.73-5.83 (m, 2H), 5.04-5.13 (m, 1H), 3.99-4.08 (m, 1H), 2.71-2.82 (m, 2H), 2.51-2.61 (m, 1H), 2.15-2.26 (m, 1H).

Workup

  1. customstored at −20° C.
  2. customsealed
  3. temperatureThe reaction mixture was cooled to room temperature
  4. concentrationconcentrated
  5. customthe residue was crystallized from hexanes

Sources & evidence

ORD record
ord-65f173634db641edb1e67c200b74ff0e
Source dataset
uspto-grants-2010_11
Patent number
US07834012B2

Reaction notes

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