Triphenylphosphine → 5-Benzoyloxy-3-chloro-1-iodo-2-[3-(5-trifluoromethylpyrid-2-yloxy)propyloxy]benzene

HRID 497051Notes

Reaction equation

HRID 497051 reaction equation
[C:1]([O:9][C:10]1[CH:11]=[C:12]([Cl:18])[C:13]([OH:17])=[C:14]([I:16])[CH:15]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:19][C:20]([F:33])([F:32])[C:21]1[CH:22]=[CH:23][C:24]([O:27][CH2:28][CH2:29][CH2:30]O)=[N:25][CH:26]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:1]([O:9][C:10]1[CH:11]=[C:12]([Cl:18])[C:13]([O:17][CH2:30][CH2:29][CH2:28][O:27][C:24]2[CH:23]=[CH:22][C:21]([C:20]([F:33])([F:19])[F:32])=[CH:26][N:25]=2)=[C:14]([I:16])[CH:15]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 112067993-{[5-(Trifluoromethyl)pyridin-2-yl]oxy}propan-1-olHCID 223186275-Benzoyloxy-3-chloro-2-hydroxy-1-iodobenzene

Product 1

HCID 223186095-Benzoyloxy-3-chloro-1-iodo-2-[3-(5-trifluoromethylpyrid-2-yloxy)propyloxy]benzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under an atmosphere of protective gas, 3.5 g of 5-benzoyloxy-3-chloro-2-hydroxy-1-iodobenzene, 2.07 g of 3-(5-trifluoromethylpyrid-2-yloxy)propan-1-ol and 2.57 g of triphenylphosphine were dissolved in 100 ml of dry tetrahydrofuran (THF). With ice-bath cooling, 1.71 g of diethyl azodicarboxylate were added dropwise. After about 30 minutes, the ice-bath was removed, and the mixture was stirred at room temperature for 15 hours. The mixture was then concentrated under reduced pressure and the residue was taken up in a mixture of ethyl acetate and water. After shaking, the organic phase was isolated, dried and concentrated under reduced pressure. The crude product was purified chromatographically. Yield: 3.12 g (58%)

Workup

  1. temperatureWith ice-bath cooling
  2. customthe ice-bath was removed
  3. concentrationThe mixture was then concentrated under reduced pressure
  4. additionthe residue was taken up in a mixture of ethyl acetate and water
  5. stirringAfter shaking
  6. customthe organic phase was isolated
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was purified chromatographically

Sources & evidence

ORD record
ord-c5d3022a10ce4d6599d3d37b72462c89
Source dataset
uspto-grants-2005_09
Patent number
US06949551B2

Reaction notes

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