Triphenylphosphine → 3-Chloro-5-[2-(4-cyanophenyl)ethoxy]phenol

HRID 1791872Notes

Reaction equation

HRID 1791872 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[Cl:32][C:33]1[CH:38]=[C:37]([OH:39])[CH:36]=[C:35]([OH:40])[CH:34]=1.[C:41]([C:43]1[CH:48]=[CH:47][C:46]([CH2:49][CH2:50]O)=[CH:45][CH:44]=1)#[N:42]>C(Cl)Cl.CCOCC>[Cl:32][C:33]1[CH:38]=[C:37]([OH:39])[CH:36]=[C:35]([O:40][CH2:50][CH2:49][C:46]2[CH:47]=[CH:48][C:43]([C:41]#[N:42])=[CH:44][CH:45]=2)[CH:34]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 945541,3-Benzenediol, 5-chloro-HCID 28008154-(2-Hydroxyethyl)benzonitrileHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 220335343-Chloro-5-[2-(4-cyanophenyl)ethoxy]phenolYield 21.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Triphenylphoshine (32 g; 122 mmol) and diethylazodicarboxylate (19.2 mL; 122 mmol) were dissolved in CH2Cl2 (150 mL). Chloro-3,5-dihydroxybenzene (9.1 g; 63 mmol; from step (i) above) and 2-(4-cyanophenyl)ethanol (9.04 g; 61 mmol) were added and the solution was stirred at room temperature overnight. The mixture was diluted with Et2O and filtered through Celite. The solvent was removed in vacuo. Purification, first by flash chromatography (SiO2; CH2Cl2:MeOH), then by preparative HPLC (60% CH3CN:0.1 M NH4OAc/aq), afforded 3.55 g (21%) of the sub-title compound.

Workup

  1. filtrationfiltered through Celite
  2. customThe solvent was removed in vacuo
  3. customPurification

Sources & evidence

ORD record
ord-62d2192aded34cdfa64452a6022fb411
Source dataset
uspto-grants-2006_07
Patent number
US07074820B2

Reaction notes

Loading…