Sodium Hydroxide → HCID 59300324, compound

HRID 2236552Notes

Reaction equation

HRID 2236552 reaction equation
Br[O-].[Na+].[OH-].[Na+].BrBr.[CH3:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][CH2:17][N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[CH:12]=[CH:11][C:10]=1[C:24](=[O:26])C.S(=O)(O)[O-:28].[Na+]>O.O1CCOCC1>[CH3:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][CH2:17][N:18]2[CH2:19][CH2:20][O:21][CH2:22][CH2:23]2)[CH:12]=[CH:11][C:10]=1[C:24]([OH:26])=[O:28]

Participants

8

Reactant 5

HCID 14798Sodium HydroxideHCID 24408BromineHCID 23665763Sodium BisulfiteHCID 23673712Sodium hypobromiteHCID 59299847HCID 59299847, compound

Product 1

HCID 59300324HCID 59300324, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

A solution of sodium hypobromite, prepared at 0° C. by dissolving sodium hydroxide (45.71 g, 1.14 mole) in water (200 mL) and bromine (16.3 mL, 0.30 mole) over 5 minutes. This solution is then added dropwise over 30 minutes to a solution of 1-[2-methyl-4-(2-morpholin-4-yl-ethoxy)-phenyl]-ethanone (19.2 g, 0.073 mole) in dioxane (140 mL), then warmed to 40° C. and stirred for 30 minutes. Sodium bisulfite is added to destroy the excess sodium hypobromite and then diluted with water (800 mL) and stirred overnight at ambient temperature. The volume is reduced in-vacuo by about 300 mL and then acidified with 3 N hydrochloric acid to pH 6. This is then extracted repeatedly with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and evaporated to give a white solid, 4.09 g (21%), MS (ESI): m/z 266.2 (M+H).

Workup

  1. customto destroy the excess sodium hypobromite
  2. additiondiluted with water (800 mL)
  3. stirringstirred overnight at ambient temperature
  4. extractionThis is then extracted repeatedly with ethyl acetate
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customto give a white solid, 4.09 g (21%), MS (ESI)

Sources & evidence

ORD record
ord-c2e8141c9e1b4d008ff2208170e4ec0b
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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