HCID 86682286, compound → HCID 86682288, compound

HRID 540463Notes

Reaction equation

HRID 540463 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH2:12][CH:13]=[CH2:14])[CH2:9]C=C)[CH:5]=[CH:4][C:3]=1[O:15][CH3:16]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([CH:8]2[CH2:9][CH:14]=[CH:13][CH2:12]2)[CH:5]=[CH:4][C:3]=1[O:15][CH3:16]

Participants

3

Reactant 1

HCID 86682286HCID 86682286, compound

Product 1

HCID 86682288HCID 86682288, compoundYield 105.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 2-bromo-4-(hepta-1,6-dien-4-yl)-1-methoxybenzene (2.0 g, 7.11 mmol) in DCM (36 mL) was added Zhan catalyst (47 mg). The mixture was flushed with N2 and refluxed at 45° C. overnight. The reaction mixture was concentrated and the residue was purified by silica gel chromatography, eluting with 10% of EtOAc/isohexane to give 2-bromo-4-(cyclopent-3-en-1-yl)-1-methoxybenzene (1.9 g) as a colorless oil. 1H NMR (500 MHz, CDCl3:) δ 7.46 (s, 1H), 7.18 (d, 1H), 6.83 (d, 1H), 5.80 (s, 2H), 3.91 (s, 3H), 3.40 (m, 1H), 2.81 (m, 2H), 2.40 (m, 2H).

Workup

  1. customThe mixture was flushed with N2
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by silica gel chromatography
  4. washeluting with 10% of EtOAc/isohexane

Sources & evidence

ORD record
ord-58cb2f22f0594390b31e7ed25784433e
Source dataset
uspto-grants-2014_10
Patent number
US08871738B2

Reaction notes

Loading…