Potassium Carbonate → 5-Bromo-2-(3-methyl-oxetan-3-ylmethoxy)-benzaldehyde

HRID 504458Notes

Reaction equation

HRID 504458 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].C([O-])([O-])=O.[K+].[K+].[CH3:17][C:18]1([CH2:22]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:21][O:20][CH2:19]1>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:17][C:18]2([CH3:22])[CH2:21][O:20][CH2:19]2)=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 728635-BromosalicylaldehydeHCID 5461213(3-Methyloxetan-3-yl)methyl 4-methylbenzenesulfonate

Product 1

HCID 594280785-Bromo-2-(3-methyl-oxetan-3-ylmethoxy)-benzaldehydeYield 50.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

To a mixture of 5-bromo-2-hydroxy-benzaldehyde (14 g, 70 mmol), KI (5 g) and K2CO3 (19 g, 140 mmol) in DMF (100 mL) was added toluene-4-sulfonic acid 3-methyl-oxetan-3-ylmethyl ester (18 g, 70 mmol). The mixture was heated at 140° C. for 2 h, and then cooled to room temperature, partitioned between water and ethyl acetate. The organic layer was washed with water for 3 times, dried over anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography to give the title compound (10 g).

Workup

  1. temperaturecooled to room temperature
  2. custompartitioned between water and ethyl acetate
  3. washThe organic layer was washed with water for 3 times
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-8af14ce387bd4231a0b217faf58a04cd
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

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