HCID 59829145, compound → HCID 59829207, compound

HRID 2061410Notes

Reaction equation

HRID 2061410 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:19]([OH:22])[CH:20]=[CH2:21])[CH:5]=[C:6]([Br:18])[C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1>C(Cl)(Cl)Cl.[O-2].[Mn+4].[O-2]>[Br:1][C:2]1[CH:3]=[C:4]([C:19](=[O:22])[CH:20]=[CH2:21])[CH:5]=[C:6]([Br:18])[C:7]=1[O:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=1

Participants

4

Reactant 1

HCID 59829145HCID 59829145, compound

Product 1

HCID 59829207HCID 59829207, compoundYield 40.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

To a stirred solution of 1-(3,5-dibromo-4-(4-methoxybenzyloxy)phenyl)prop-2-en-1-ol (D) (2.45 g, 5.73 mmol) in chloroform (35 mL) under nitrogen was added manganese(IV) oxide (6.47 g, 74.4 mmol) and the mixture was stirred vigorously for 2 h. The mixture was filtered through glass fibre paper and the solid was washed with more chloroform (5×15 mL). The combined filtrates were evaporated and the residue was purified by flash chromatography (silica gel, 15% EtOAc/pet. ether) to afford 0.9804 g (40%) of the title compound as a white solid. 1H NMR δ (ppm) (CDCl3): 3.84 (3 H, s), 5.04 (2 H, s), 5.99 (1 H, dd, J=10.56, 1.51 Hz), 6.47 (1 H, dd, J=17.06, 1.52 Hz), 6.91-6.97 (2 H, m), 7.07 (1 H, dd, J=17.06, 10.57 Hz), 7.52 (2 H, d, J=8.41 Hz), 8.12 (2 H, s).

Workup

  1. filtrationThe mixture was filtered through glass fibre paper
  2. washthe solid was washed with more chloroform (5×15 mL)
  3. customThe combined filtrates were evaporated
  4. customthe residue was purified by flash chromatography (silica gel, 15% EtOAc/pet. ether)

Sources & evidence

ORD record
ord-dd87879d405541c0a3be8e5d0e036ad8
Source dataset
uspto-grants-2012_10
Patent number
US08283351B2

Reaction notes

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