Water → HCID 86049356, compound

HRID 1160087Notes

Reaction equation

HRID 1160087 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1)=O.O.Cl.[O:14]([NH2:16])[CH3:15]>CO>[CH3:15][O:14][N:16]=[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][CH:6]=1)[CH2:2][Br:1]

Participants

5

Reactant 3

HCID 962WaterHCID 692722-Bromo-4'-methylacetophenoneHCID 521874O-Methylhydroxylamine hydrochloride

Product 1

HCID 86049356HCID 86049356, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-bromo-4′-methyl-acetophenone (6.514 g, 27.5 mmol) in methanol at 50° C. was added water until the solution turned slightly cloudy. Methoxylamine hydrochloride (7.037, 85.7 mmol) was added and the mixture was stirred overnight. The solvent was removed under high vacuum and the residue was extracted with EtOAc and dried over MgSO4. The product was purified by flash chromatography on silicagel (CH2Cl2/hexanes) to give 2 isomers in 87% total yield: 2 isomers in 87% total yield: Z-isomer 1H NMR 500 MHz (DMSO-d6) δ 2.33 (s, 3H), 3.83 (s, 3H), 4.62 (s, 2H), 7.26 (dd, 2H, J=1.8, 8.2 Hz), 7.51 (d, 2H, J=7.6 Hz); FABHRMS: found M+, 242.0177 (calcd for C10H13ONBr: M+, 242.0175). E-isomer 1H-NMR 500 MHz (DMSO-d6) d 2.33 (s, 3H), 3.99 (s, 3H), 4.68 (s, 2H), 7.25 (d, 2H, J=8.2 Hz), 7.61 (d, 2H, J=7.3 Hz); FABHRMS: found M+, 242.0175 (calcd for C10H13ONBr: M+, 242.0175).

Workup

  1. customThe solvent was removed under high vacuum
  2. extractionthe residue was extracted with EtOAc
  3. dry with materialdried over MgSO4
  4. customThe product was purified by flash chromatography on silicagel (CH2Cl2/hexanes)
  5. customto give 2 isomers in 87% total yield

Sources & evidence

ORD record
ord-1c86df953c414522b3d968bdb56f684c
Source dataset
uspto-grants-2010_10
Patent number
US07816352B2

Reaction notes

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