HCID 86724236, compound → 3-((4-Bromo-2-iodophenoxy)methyl)-6-chlorohex-1-en-3-ol

HRID 873704Notes

Reaction equation

HRID 873704 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH2:7][C:8](=[O:13])[CH2:9][CH2:10][CH2:11][Cl:12])=[C:4]([I:16])[CH:3]=1.[CH:17]([Mg]Br)=[CH2:18]>C1COCC1>[Br:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][CH2:7][C:8]([OH:13])([CH2:9][CH2:10][CH2:11][Cl:12])[CH:17]=[CH2:18])=[C:4]([I:16])[CH:3]=1

Participants

4

Reactant 2

HCID 86724236HCID 86724236, compoundHCID 178418507HCID 178418507, compound

Product 1

HCID 867242453-((4-Bromo-2-iodophenoxy)methyl)-6-chlorohex-1-en-3-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 1-(4-bromo-2-iodophenoxy)-5-chloropentan-2-one (1.61 g, 3.86 mmol) in THF (35 mL) was added vinylmagnesium bromide (1M solution in THF, 4.3 mL) at −78° C. under an argon atmosphere. After stirring for 1 hour at −78° C., the mixture was gradually warmed up to −30° C. over 1 hour. The reaction was quenched by adding saturated aqueous NH4Cl solution and extracted with EtOAc. The combined organic layer were washed with brine, dried over Na2SO4, filtered, and the filtrate was evaporated. The residue was purified by silicagel column chromatography (EtOAc-hexane, a linear gradient of EtOAc from 0 to 20%) afforded 3-[(4-bromo-2-iodophenoxy)methyl]-6-chlorohex-1-en-3-ol (1.35 g).

Workup

  1. temperaturethe mixture was gradually warmed up to −30° C. over 1 hour
  2. customThe reaction was quenched
  3. additionby adding saturated aqueous NH4Cl solution
  4. extractionextracted with EtOAc
  5. washThe combined organic layer were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customthe filtrate was evaporated
  9. customThe residue was purified by silicagel column chromatography (EtOAc-hexane

Sources & evidence

ORD record
ord-cbd9be2fbbc74c7e8ed4bd81a35370a0
Source dataset
uspto-grants-2015_03
Patent number
US08975415B2

Reaction notes

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