2-Bromoethanol → HCID 28897766, compound

HRID 877316Notes

Reaction equation

HRID 877316 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:5]([OH:14])=[C:6]([O:12][CH3:13])[CH:7]=[C:8]([CH:11]=1)[CH:9]=[O:10].Br[CH2:16][CH2:17][OH:18]>CN(C=O)C.C(OCC)(=O)C>[Cl:3][C:4]1[CH:11]=[C:8]([CH:7]=[C:6]([O:12][CH3:13])[C:5]=1[O:14][CH2:16][CH2:17][OH:18])[CH:9]=[O:10]

Participants

6

Reactant 3

HCID 108982-BromoethanolHCID 24758Sodium hydrideHCID 296223-Chloro-4-hydroxy-5-methoxybenzaldehyde

Product 1

HCID 28897766HCID 28897766, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of sodium hydride (60% dispersion in mineral oil, 0.24 g, 6.00 mmol) in DMF (8 mL) was added a solution of 5-chlorovanillin (0.746 g, 4.00 mmol) in DMF (2 mL). The reaction mixture was stirred at RT for 20 minutes and 2-bromoethanol (0.42 mL, 5.93 mmol) added. The reaction mixture was heated at 50° C. for 90 hours. The reaction mixture was diluted with ethyl acetate and washed with water, brine (×2), dried (magnesium sulfate), filtered and the solvent evaporated at reduced pressure. The residue was purified by flash column chromatography eluting with 0-50% ethyl acetate in iso-hexane to afford the title compound (0.413 g, 48%).

Workup

  1. temperatureThe reaction mixture was heated at 50° C. for 90 hours
  2. washwashed with water, brine (×2)
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. customthe solvent evaporated at reduced pressure
  6. customThe residue was purified by flash column chromatography
  7. washeluting with 0-50% ethyl acetate in iso-hexane

Sources & evidence

ORD record
ord-a2fcdf3ad2a34c5d8ef81dc32484dd47
Source dataset
uspto-grants-2015_03
Patent number
US08987299B2

Reaction notes

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