Bromide ion → HCID 21105423, compound

HRID 2426733Notes

Reaction equation

HRID 2426733 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:14](=[O:16])C)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:13])[CH2:10][CH2:11][CH3:12].[OH-].[Na+].BrBr.[Br-].S(OS([O-])=O)([O-])=[O:23].[Na+].[Na+].Cl>O1CCOCC1.O>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:13])[CH2:10][CH2:11][CH3:12])[C:14]([OH:16])=[O:23]

Participants

9

Reactant 6

HCID 259Bromide ionHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24346Disodium disulfiteHCID 24408BromineHCID 21105303HCID 21105303, compound

Product 1

HCID 21105423HCID 21105423, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 0.449 g of 1-[3-fluoro-4-(1-methylbutoxy)phenyl]ethanone in 6.8 ml of dioxane was dropped dropwise into 1.36 g of NaOH, 1.6 g of bromine in 6.8 ml of water. The mixture was stirred at room temperature for 30 minutes and then heated at 50° C. for 1 h. The excess bromide was decomposed by adding a sodium disulfite solution, and then the solution was poured into 25% strength hydrochloric acid solution and stirred for 20 minutes. The solution was extracted with ethyl acetate. The combined organic phases dried over sodium sulfate, concentrated in vacuo and purified by preparative HPLC. This resulted in the product with the molecular weight of 226.1 (C12H15FO3); MS (ESI): 227 (M+H+).

Workup

  1. temperatureheated at 50° C. for 1 h
  2. stirringstirred for 20 minutes
  3. extractionThe solution was extracted with ethyl acetate
  4. dry with materialThe combined organic phases dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. custompurified by preparative HPLC
  7. customThis resulted in the product with the molecular weight of 226.1 (C12H15FO3)

Sources & evidence

ORD record
ord-6211f177653f425e86645b67d5dd3f6e
Source dataset
uspto-grants-2011_06
Patent number
US07968550B2

Reaction notes

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