1-(4-Iodophenyl)ethan-1-one → HCID 71145829, compound

HRID 535305Notes

Reaction equation

HRID 535305 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([I:10])=[CH:6][CH:5]=1)=[O:3].[CH3:11][O:12][C:13]1[CH:14]=[C:15]([Mg]Br)[CH:16]=[CH:17][CH:18]=1>C1COCC1>[I:10][C:7]1[CH:8]=[CH:9][C:4]([C:2]([C:17]2[CH:16]=[CH:15][CH:14]=[C:13]([O:12][CH3:11])[CH:18]=2)([OH:3])[CH3:1])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 728691-(4-Iodophenyl)ethan-1-oneHCID 178490745HCID 178490745, compound

Product 1

HCID 71145829HCID 71145829, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-iodoacetophenone (2 g, 7.97 mmol) in THF (20 ml) was immersed in an ice-bath and (3-methoxyphenyl)magnesium bromide 1M in THF (23.90 ml, 23.90 mmol) was added slowly by syringe. The reaction mixture was stirred at r.t. for 3 hrs. The reaction mixture was quenched with 20 ml aqueous saturated NH4Cl solution and diluted with ethyl acetate. The organic phase was separated and washed with brine. The organic phase was dried over Na2SO4, filtered and concentrated in vacuo to obtain the crude product which was purified by automated column chromatography (n-heptane (isom. mixture)/ethyl acetate). Organic solvents were removed to obtain title compound as yellowish oil.

Workup

  1. customThe reaction mixture was quenched with 20 ml aqueous saturated NH4Cl solution
  2. additiondiluted with ethyl acetate
  3. customThe organic phase was separated
  4. washwashed with brine
  5. dry with materialThe organic phase was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto obtain the crude product which
  9. customwas purified by automated column chromatography (n-heptane (isom. mixture)/ethyl acetate)
  10. customOrganic solvents were removed

Sources & evidence

ORD record
ord-ad60ea66fbb84fabafd3f8657ce3f420
Source dataset
uspto-grants-2014_10
Patent number
US08859535B2

Reaction notes

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