4-Iodophenol → 5-[(4-Iodophenoxy)methyl]bicyclo[2.2.1]hept-2-ene

HRID 7328

Reaction equation

HRID 7328 reaction equation
CCOC(/N=N/C(OCC)=O)=O.[CH:13]12[CH2:19][CH:16]([CH:17]=[CH:18]1)[CH2:15][CH:14]2[CH2:20][OH:21].[I:22][C:23]1[CH:28]=[CH:27][C:26](O)=[CH:25][CH:24]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[I:22][C:23]1[CH:28]=[CH:27][C:26]([O:21][CH2:20][CH:14]2[CH2:15][CH:16]3[CH2:19][CH:13]2[CH:18]=[CH:17]3)=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 108944-IodophenolHCID 11776TriphenylphosphineHCID 78946Bicyclo(2.2.1)hept-5-ene-2-methanolHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 219893005-[(4-Iodophenoxy)methyl]bicyclo[2.2.1]hept-2-eneYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethylazodicarboxylate (8.7 g) was added dropwise to a solution of 5-norbornene-2-methanol (6.2 g, 0.05 mol), 4-iodophenol (11.0 g, 0.05 mol) and triphenylphosphine (13.1 g, 0.05 mol) in 100 mL of anhydrous tetrahydrofuran. After completion of the addition, the resulting solution was stirred for 18 h at room temperature. The solvent was removed under reduced pressure and the oily residue was extracted three times with hot hexane. Combined hexane extracts were evaporated under reduced pressure to give 8 (15.0 g, 97%) as a colorless oil.

Workup

  1. additionAfter completion of the addition
  2. customThe solvent was removed under reduced pressure
  3. extractionthe oily residue was extracted three times with hot hexane
  4. customCombined hexane extracts were evaporated under reduced pressure

Sources & evidence

ORD record
ord-fe246bcbccfc45eab97f443429b20fe3
Source dataset
uspto-grants-2006_08
Patent number
US07087267B2

Linked notes

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