Methanol → HCID 86666944, compound

HRID 2274120Notes

Reaction equation

HRID 2274120 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([C:9](=[O:11])[CH3:10])=[C:4]([OH:12])[C:3]=1[I:13].[C:14]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CO.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([C:9](=[O:11])[CH3:10])=[C:4]([O:12][CH3:14])[C:3]=1[I:13]

Participants

6

Reactant 4

HCID 887MethanolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 86666943HCID 86666943, compound

Product 1

HCID 86666944HCID 86666944, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 1-(4,5-dichloro-2-hydroxy-3-iodophenyl)ethanone (4.9 g, 15 mmol), triphenylphosphine (5.5 g, 21 mmol), and methanol (0.91 mL, 22 mmol) in tetrahydrofuran (44 mL) at 0° C. was treated with diisopropyl azodicarboxylate (4.1 mL, 21 mmol) dropwise and stirred at 20° C. for 16 h. The reaction mixture was concentrated, diluted with ethyl acetate, and poured into water. The organic layer was separated, washed with brine, dried with magnesium sulfate, filtered, and concentrated to a crude residue. Purification by flash column chromatography using ethyl acetate in hexanes (5%-30%) gave the desired product (4.1 g, 79%). LCMS for C9H8Cl2IO2 (M+H)+: m/z=344.9, 346.9. Found: 344.9, 346.7.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with ethyl acetate
  3. additionpoured into water
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to a crude residue
  9. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-dab5367458c04388b1756d4957a20792
Source dataset
uspto-grants-2015_09
Patent number
US09126948B2

Reaction notes

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