Water → HCID 86677773, compound

HRID 1499849Notes

Reaction equation

HRID 1499849 reaction equation
[Br:1][C:2]1[C:3]([OH:13])=[C:4]([C:10](=[O:12])[CH3:11])[CH:5]=[C:6]([Cl:9])[C:7]=1[CH3:8].C(=O)([O-])[O-].[K+].[K+].I[CH2:21][CH3:22].O>CN(C=O)C>[Br:1][C:2]1[C:3]([O:13][CH2:21][CH3:22])=[C:4]([C:10](=[O:12])[CH3:11])[CH:5]=[C:6]([Cl:9])[C:7]=1[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 120274791-(3-Bromo-5-chloro-2-hydroxy-4-methylphenyl)ethanone

Product 1

HCID 86677773HCID 86677773, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Into a round bottom flask was placed 1-(3-bromo-5-chloro-2-hydroxy-4-methylphenyl)ethanone (6.0 g, 23 mmol) in anhydrous DMF (22.8 mL). Potassium carbonate (6.3 g, 46 mmol) was then added followed by iodoethane (2.73 mL, 34.2 mmol). The resulting suspension was stirred at 60° C. for 2 h. The mixture was poured into 100 mL water and extracted with 200 mL of ethyl ether. The organic layers were separated, combined and washed with water and saturated NaCl solution, dried over anhydrous sodium sulfate, filtered, and concentrated to 6.0 g of tan oil. LCMS calculated for C11H13BrClO2 (M+H)+: m/z=293.0; Found: 293.0

Workup

  1. customInto a round bottom flask was placed
  2. extractionextracted with 200 mL of ethyl ether
  3. customThe organic layers were separated
  4. washwashed with water and saturated NaCl solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to 6.0 g of tan oil

Sources & evidence

ORD record
ord-7a3c4c502f1b4296b96da04029e9da52
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

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