Water → 7-Bromo-5-methoxy-1-benzofuran

HRID 920121Notes

Reaction equation

HRID 920121 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[O:10][CH2:11][CH:12](OCC)OCC.O.[OH-].[Na+]>C1(C)C=CC=CC=1.CCOC(C)=O>[Br:1][C:2]1[C:3]2[O:10][CH:11]=[CH:12][C:4]=2[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 896563492-Bromo-1-(2,2-diethoxyethoxy)-4-methoxybenzene

Product 1

HCID 221447037-Bromo-5-methoxy-1-benzofuranYield 16%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of the product from step B (2.7 g, 8.5 mmol) in toluene (10 mL) was added PPA (1.0 mL). The reaction was heated at 70° C. for 1 hr. The reaction was cooled to room temperature. The mixture was diluted with EtOAc (200 mL) and the water phase was adjusted to pH 7-8 by NaOH (2 mol/L). The organic phase was washed with brine (50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica column chromatography (eluted with PE) to afford the title compound (0.27 g, 16%) as an oil. 1H-NMR (600 MHz, CDCl3) δ 7.68 (d, J=2.1 Hz, 1H), 7.13 (d, J=2.2 Hz, 1H), 7.04 (d, J=2.3 Hz, 1H), 6.79 (d, J=2.1 Hz, 1H), 3.86 (s, 3H) ppm.

Workup

  1. additionwas added PPA (1.0 mL)
  2. temperatureThe reaction was cooled to room temperature
  3. washThe organic phase was washed with brine (50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica column chromatography (eluted with PE)

Sources & evidence

ORD record
ord-57ec875d33f54856a41e31424a6b952e
Source dataset
uspto-grants-2016_03
Patent number
US09273046B2

Reaction notes

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