Triphenylphosphine → HCID 68769064, compound

HRID 1170415Notes

Reaction equation

HRID 1170415 reaction equation
[C:1]1([C:7]2[O:8][C:9]3[CH:15]=[CH:14][C:13]([CH2:16][CH2:17]O)=[CH:12][C:10]=3[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C(=O)N([I:26])C(=O)C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[I:26][CH2:17][CH2:16][C:13]1[CH:14]=[CH:15][C:9]2[O:8][C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:11][C:10]=2[CH:12]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 120273N-IodosuccinimideHCID 68769027HCID 68769027, compound

Product 1

HCID 68769064HCID 68769064, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(2-Phenyl-benzofuran-5-yl)ethanol (11.18 g; 46.9 mmol) was dissolved in DCM (170 ml) and N-iodinesuccinimide (NIS; 11.31 g; 50.27 mmol) and triphenylphosphine (15.39 g; 52.67 mmol) was added under stirring. After keeping the reaction mixture at RT over night the reaction was extracted two times with 6% aqueous NaHCO3 solution and the organic layer was dried over Na2SO4. After filtering and removal of the solvent pure title compound was obtained after crystallization from methanol/DCM/cyclo-hexane. The mother liquor was collected and purified on silica gel (cyclohexane/ethylacetate 95/5 as mobile phase).

Workup

  1. customat RT
  2. extractionwas extracted two times with 6% aqueous NaHCO3 solution
  3. dry with materialthe organic layer was dried over Na2SO4
  4. filtrationAfter filtering
  5. customremoval of the solvent pure title compound
  6. customwas obtained
  7. customafter crystallization from methanol/DCM/cyclo-hexane
  8. customThe mother liquor was collected
  9. custompurified on silica gel (cyclohexane/ethylacetate 95/5 as mobile phase)

Sources & evidence

ORD record
ord-4ba8080ee9b64b3093db95dc43daf49e
Source dataset
uspto-grants-2010_11
Patent number
US07825260B2

Reaction notes

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