Potassium Carbonate → 5-Bromo-2-[(2R)-oxiran-2-ylmethoxy]benzaldehyde

HRID 38992

Reaction equation

HRID 38992 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH2:11](OS(C1C=CC(C)=CC=1)(=O)=O)[C@@H:12]1[O:14][CH2:13]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][C@H:12]2[CH2:13][O:14]2)=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 728635-BromosalicylaldehydeHCID 154187Glycidyl tosylate, (R)-

Product 1

HCID 541570455-Bromo-2-[(2R)-oxiran-2-ylmethoxy]benzaldehydeYield 91.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Preparation according to Preparation 1 using 5-bromo-2-hydroxybenzaldehyde (6 g, 29 mmol), (R)-glycidyltosylate (6.7 g, 29 mmol), K2CO3 (4.9 g, 35 mmol) and DMF (12 ml). The combined organic phases were washed with LiCl (5%, 100 ml), HCl (1 N, 100 ml), brine (100 ml) and were evaporated to dryness. The residue was purified by flash column chromatography (isooctane/EtOAc) to give the crude title compound (6.8 g). MS m/z (rel. intensity, 70 eV) 257 (M+, 38), 256 (M+, 39), 200 (bp), 199 (87), 57 (88).

Workup

  1. customPreparation
  2. washThe combined organic phases were washed with LiCl (5%, 100 ml), HCl (1 N, 100 ml), brine (100 ml)
  3. customwere evaporated to dryness
  4. customThe residue was purified by flash column chromatography (isooctane/EtOAc)

Sources & evidence

ORD record
ord-d57b1b6bb37145008773e9440c539675
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Linked notes

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