Methyl morpholine oxide → 2-Chloro-5-(2-methoxyethoxy)benzaldehyde

HRID 561795Notes

Reaction equation

HRID 561795 reaction equation
Br[CH2:2][C:3]1[CH:8]=[C:7]([O:9][CH2:10][CH2:11][O:12][CH3:13])[CH:6]=[CH:5][C:4]=1[Cl:14].C[N+]1([O-])CC[O:19]CC1>O1CCOCC1.[Cl-].[Na+].O>[Cl:14][C:4]1[CH:5]=[CH:6][C:7]([O:9][CH2:10][CH2:11][O:12][CH3:13])=[CH:8][C:3]=1[CH:2]=[O:19]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 591775552-(Bromomethyl)-1-chloro-4-(2-methoxyethoxy)benzene

Product 1

HCID 866359132-Chloro-5-(2-methoxyethoxy)benzaldehyde

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-(bromomethyl)-1-chloro-4-(2-methoxyethoxy)benzene from the previous step (1 eq.) in dioxane (0.2 M) was added 4-methylmorpholine N-oxide (3 eq.). The reaction mixture was heated at 80° C. The resulting solution was allowed to cool to RT, poured into brine and then extracted with EtOAc. The combined organic extracts were dried over MgSO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of flash chromatography (SiO2, Hex→2:1 (v/v) Hex:EtOAc) afforded the title compound as a pale yellow oil.

Workup

  1. temperatureto cool to RT
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated in vacuo
  6. customPurification of the crude product
  7. customthus obtained by way of flash chromatography (SiO2, Hex→2:1 (v/v) Hex:EtOAc)

Sources & evidence

ORD record
ord-aafbd440ab6d41eaac148878ced3f83c
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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