Water → HCID 67514886, compound

HRID 1754331Notes

Reaction equation

HRID 1754331 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9](=O)[CH:10]=[C:11]([CH3:13])[CH3:12])[CH:5]=[CH:6][C:7]=1[CH3:8].Cl.[NH2:16][OH:17].[OH-].[K+].O>C(O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[CH2:10][C:11]([CH3:13])([CH3:12])[O:17][N:16]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

7

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 86694673HCID 86694673, compound

Product 1

HCID 67514886HCID 67514886, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 1-(3-bromo-4-methylphenyl)-3-methylbut-2-en-1-one, (prepared herein before in step 2 of intermediate 1; 1.0 g, 3.95 mmol, 1.0 eq), and hydroxylamine hydrochloride (330 mg, 4.74 mmol, 1.2 eq) in ethanol (10 mL) at 0° C., was added an aqueous solution of potassium hydroxide (1N, 4 mL) until the pH of the reaction was basic. The resulting mixture was stirred at room temperature for 4 h. The reaction mixture was diluted with ethyl acetate (20 mL) followed by water (20 mL). The layers were separated and the organic layer was extracted with ethyl acetate (2×20 mL). The combined organic layers were washed with brine (20 mL), dried (Na2SO4) and filtered. The filtrate was concentrated under vacuum. The crude product was purified by flash column chromatography (silica gel, 5% EtOAc in hexane) to afford 250 mg of the desired product as a white solid. 1HNMR (400 MHz, CDCl3) δ 7.79 (s, 1H), 7.53 (d, J=8.0 Hz, 1H), 7.27 (d, J=8.0 Hz, 1H), 3.08 (s, 2H), 2.43 (s, 3H), 1.50 (s, 6H); ESI-MS (m/z) 268, 270 [(MH)+, Br79,81].

Workup

  1. customThe layers were separated
  2. extractionthe organic layer was extracted with ethyl acetate (2×20 mL)
  3. washThe combined organic layers were washed with brine (20 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% EtOAc in hexane)

Sources & evidence

ORD record
ord-f81171465dfd468fbbbd6970437932e1
Source dataset
uspto-grants-2015_10
Patent number
US09169242B2

Reaction notes

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