Hydrochloric Acid → 6-Bromo-2-ethyl-3-o-tolyl-4H-chromen-4-one

HRID 1484298Notes

Reaction equation

HRID 1484298 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:18])=[C:6]([C:8](=[O:17])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16])[CH:7]=1.[C:19](OC(=O)CC)(=O)[CH2:20][CH3:21].Cl>C(N(CC)CC)C>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:18][C:19]([CH2:20][CH3:21])=[C:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16])[C:8]2=[O:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31263Propionic anhydrideHCID 532343631-(5-Bromo-2-hydroxyphenyl)-2-o-tolylethanone

Product 1

HCID 602090526-Bromo-2-ethyl-3-o-tolyl-4H-chromen-4-oneYield 20.7%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Intermediate 11 (3.0 g, 9.83 mmoles) was taken in a RB flask and to this triethylamine (25 ml) and propionic anhydride (4.00 g, 30.76 mmoles) were added and the mixture was refluxed for 24 h. After cooling to RT, the reaction mixture was acidified by the addition of 1N HCl solution, extracted with ethyl acetate, washed with sodium bicarbonate solution, dried with sodium sulphate and concentrated. The crude product was purified by column chromatography with ethyl acetate:petroleum ether to afford the title compound as colourless liquid (0.700 g, 20% yield). 1H-NMR (δ ppm, DMSO-d6, 400 MHz): δ 7.73 (d, J=2.5 Hz, 1H), 7.63 (dd, J=8.7, 2.5 Hz, 1H), 7.34 (t, J=4.8 Hz, 1H), 7.22-7.14 (m, 4H), 2.63 (q, J=7.5 Hz, 2H), 0.94 (t, J=7.5 Hz, 3H).

Workup

  1. additionwere added
  2. temperaturethe mixture was refluxed for 24 h
  3. extractionextracted with ethyl acetate
  4. washwashed with sodium bicarbonate solution
  5. dry with materialdried with sodium sulphate
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography with ethyl acetate

Sources & evidence

ORD record
ord-b65e2b516f164ae49d4a82aec21f9417
Source dataset
uspto-grants-2016_08
Patent number
US09421209B2

Reaction notes

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