Ethyl Bromide → HCID 86664745, compound

HRID 2368011Notes

Reaction equation

HRID 2368011 reaction equation
[CH2:1](Br)[CH3:2].[Br:4][C:5]1[C:12]([OH:13])=[C:11]([O:14][CH3:15])[CH:10]=[CH:9][C:6]=1[CH:7]=[O:8].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOC(C)=O>[Br:4][C:5]1[C:12]([O:13][CH2:1][CH3:2])=[C:11]([O:14][CH3:15])[CH:10]=[CH:9][C:6]=1[CH:7]=[O:8]

Participants

6

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 2240112-Bromoisovanillin

Product 1

HCID 86664745HCID 86664745, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
35 °C

Procedure

Ethyl bromide (2.88 g, 26.4 mmol) was added to a mixture of 2-bromo-3-hydroxy-4-methoxybenzaldehyde (5.08 g, 22 mmol) and potassium carbonate (4.56 g, 33 mmol) in anhydrous DMF (50 mL) at room temperature under nitrogen. The reaction mixture was stirred at 35° C. for 18 h, diluted with EtOAc (150 mL), washed with water (2×50 mL), brine, dried over Na2SO4 and concentrated to give crude product as a white solid. Purification by silica column chromatography (eluant: 30% EtOAc in Hexanes) to generate 5.65 g (99% yield) of the title compound as a white solid. 1H NMR (400 MHz, CDCl3) δ (ppm) 10.26 (s, 1H), 7.73 (d, J=8.4 Hz, 1H), 6.95 (d, J=8.8 Hz, 1H), 4.08 (q, J=7.1 Hz, 2H), 3.95 (s, 3H), 1.46 (t, J=7.0 Hz, 3H); MS (ESI) m/z=261 (M+1, positive).

Workup

  1. washwashed with water (2×50 mL), brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customto give crude product as a white solid
  5. customPurification by silica column chromatography (eluant: 30% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-aba1a4a278ed4f35928d6ac89180382e
Source dataset
uspto-grants-2014_04
Patent number
US08703742B2

Reaction notes

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