Water → 3-(6-Bromo-2,3-dimethoxy-phenoxymethyl)-3-methoxymethyl-oxetane

HRID 2171053Notes

Reaction equation

HRID 2171053 reaction equation
Br[CH2:2][C:3]1([CH2:7][O:8][CH3:9])[CH2:6][O:5][CH2:4]1.[Br:10][C:11]1[C:16]([OH:17])=[C:15]([O:18][CH3:19])[C:14]([O:20][CH3:21])=[CH:13][CH:12]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Br:10][C:11]1[C:16]([O:17][CH2:2][C:3]2([CH2:7][O:8][CH3:9])[CH2:6][O:5][CH2:4]2)=[C:15]([O:18][CH3:19])[C:14]([O:20][CH3:21])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 139408076-Bromo-2,3-dimethoxyphenolHCID 674637643-(Bromomethyl)-3-(methoxymethyl)oxetane

Product 1

HCID 674658773-(6-Bromo-2,3-dimethoxy-phenoxymethyl)-3-methoxymethyl-oxetane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

3-(bromomethyl)-3-(methoxymethyl)oxetane (0.35 g, 0.18 mmol) preparation described in example 24) and 6-bromo-2,3-dimethoxyphenol (0.21 g, 0.9 mmol) (preparation described in Preparation 1) were dissolved in DMF (8 mL). K2CO3 (0.31 g, 2.2 mmol) was added. The suspension was heated in a microwave oven at 100° C. for 10 min. H2O was added and the mixture was extracted with EtOAc (×2). The combined organic phases were washed with brine, dried (Na2SO4), filtered and concentrated. Purification by flash chromatography (Heptane:EtOAc 100:0->75:25) yielded 3-(6-Bromo-2,3-dimethoxy-phenoxymethyl)-3-methoxymethyl-oxetane as an oil.

Workup

  1. extractionthe mixture was extracted with EtOAc (×2)
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography (Heptane:EtOAc 100:0->75:25)

Sources & evidence

ORD record
ord-ed9ac1165aae45edba32c7016afa7614
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

Loading…