Water → HCID 86694672, compound

HRID 1754322Notes

Reaction equation

HRID 1754322 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9](=[O:14])[CH:10]=[C:11]([CH3:13])[CH3:12])[CH:5]=[CH:6][C:7]=1[CH3:8].ClC1C=CC=C(C(OO)=[O:23])C=1.O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:9]([CH:10]2[C:11]([CH3:12])([CH3:13])[O:23]2)=[O:14])[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 86694673HCID 86694673, compound

Product 1

HCID 86694672HCID 86694672, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled solution (at 0° C.) of 1-(3-bromo-4-methylphenyl)-3-methylbut-2-en-1-one (1.50 g, 5.92 mmol, 1.0 eq) in DCM (100 mL), m-chloroperbenzoic acid (77%, 4.30 g, 17.78 mmol, 3.0 eq) was added portion wise and then allowed to warm to room temperature. After stirring for 12 h at room temperature water was added to the reaction mixture and the layers were separated. The organic layer was washed with saturated aqueous solution of sodium bicarbonate (3×50 mL) followed by brine (50 mL) and then dried (Na2SO4) and filtered. The filtrate was concentrated under vacuum. The crude product was purified by flash column chromatography (silica gel, 5% ethyl acetate in hexane) to afford 1.60 g of the desired product, as a white solid. 1HNMR (400 MHz, CDCl3) δ 8.13 (d, J=1.5 Hz, 1H), 7.81 (dd, J=1.5, 8.0 Hz, 1H), 7.36 (d, J=8.0 Hz, 1H), 3.99 (s, 1H), 2.47 (s, 3H), 1.58 (s, 3H), 1.23 (s, 3H); ESI-MS (m/z) 269, 271 [(MH)+, Br79,81].

Workup

  1. additionwas added to the reaction mixture
  2. customthe layers were separated
  3. washThe organic layer was washed with saturated aqueous solution of sodium bicarbonate (3×50 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under vacuum
  7. customThe crude product was purified by flash column chromatography (silica gel, 5% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-6258b05c89824fb19f6ad38a54bc2c47
Source dataset
uspto-grants-2015_10
Patent number
US09169242B2

Reaction notes

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