2-Iodophenol → HCID 67206796, compound

HRID 1023845Notes

Reaction equation

HRID 1023845 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[F:9][C:10]([F:21])([F:20])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][CH2:18]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:18][CH2:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:10]([F:9])([F:20])[F:21]

Participants

6

Reactant 4

HCID 107842-IodophenolHCID 11776TriphenylphosphineHCID 587845o-(Trifluoromethyl)phenethyl alcoholHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 67206796HCID 67206796, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of the 2-iodophenol (220.0 mg, 1.0 mmol), the 2-(2-(trifluoromethyl)phenyl)ethanol (228.0 mg, 1.2 mmol), and triphenyl phosphine (314.0 mg, 1.2 mmol) in anhydrous THF (5 mL) at 0° C. was added DEAD (40% in toluene, 1.20 mmol, 0.35 mL) dropwise. The yellow solution was allowed to warm to room temperature and stirring was continued overnite. After evaporating the solvent under reduced pressure the crude residue was dissolved in DCM (15 mL). The organic layer was washed with 10% NaOH (2×10 mL), water and brine. The organic phase was dried (Na2SO4), filtered and evaporated under reduced pressure. The crude residue was purified by column chromatography on silica gel using hexanes/EtOAc as the eluent. The compound was isolated in 56% yield as a white solid. 1H NMR: 3.17 (t, 2H, J=6.8 Hz), 4.22 (t, 2H, J=6.8 Hz), 6.90-7.10 (m, 4H), 7.15-7.23 (m 1H), 7.30-7.45 (m, 2H), 7.74 (dd, 1H, J=7.6, 1.6 Hz).

Workup

  1. customAfter evaporating the solvent under reduced pressure the crude residue
  2. dissolutionwas dissolved in DCM (15 mL)
  3. washThe organic layer was washed with 10% NaOH (2×10 mL), water and brine
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe crude residue was purified by column chromatography on silica gel
  8. customThe compound was isolated in 56% yield as a white solid

Sources & evidence

ORD record
ord-877d5f5a1a9a468c93bfb2ec00ff8b39
Source dataset
uspto-grants-2014_05
Patent number
US08722720B2

Reaction notes

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