HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Iodoethane → HCID 58572422, compound

HRID 1920805
Notes
Print preview

Reaction equation

HRID 1920805 reaction equation
[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].C(=O)([O-])[O-].[K+].[K+].[CH2:18](I)[CH3:19].C(OCC)(=O)C.CCCCCC>CN(C)C=O.O>[Br:1][C:2]1[C:7]([O:8][CH2:18][CH3:19])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 21226206Ethyl acetate hexaneHCID 232169621-(2-Bromo-3-hydroxyphenyl)ethanone

Product 1

HCID 58572422HCID 58572422, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent

Procedure

Under a nitrogen atmosphere, 1-(2-bromo-3-hydroxy phenyl)ethanone (6.50 g, 30.2 mmol), which had been obtained in Reference example 3 (3c), and potassium carbonate (8.36 g, 60.5 mmol) were dissolved in N,N-dimethyl formamide (60 mL), and stirred at room temperature for 10 minutes. Subsequently, ethyl iodide (3.14 mL, 39.3 mmol) was added to the mixture, which was then further stirred for 21 hours. Ethyl acetate/hexane (1:1, V/V) and water were added to the reaction solution for fractionation, and the aqueous layer was extracted with ethyl acetate/hexane (1:1, V/V). The organic layers were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate, 100:0-85:15, V/V) to give the title compound as a colorless oily substance (4.89 g, yield 67%).

Workup

  1. stirringwas then further stirred for 21 hours
  2. extractionthe aqueous layer was extracted with ethyl acetate/hexane (1:1, V/V)
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate, 100:0-85:15, V/V)

Sources & evidence

ORD record
ord-a810acda1e1f46a8b78d389a642e62af
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08173631B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes