Triphenylphosphine → 4-(3,4-Dichlorobenzyloxy)-3-fluorobenzaldehyde

HRID 1515104Notes

Reaction equation

HRID 1515104 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].[Cl:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[Cl:20])[CH2:15]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[Cl:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[Cl:20])[CH2:15][O:10][C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=1[F:1]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 157283,4-Dichlorobenzyl alcoholHCID 5872503-Fluoro-4-hydroxybenzaldehydeHCID 66777355Diethylazodicarboxylate toluene

Product 1

HCID 866517504-(3,4-Dichlorobenzyloxy)-3-fluorobenzaldehydeYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Fluoro-4-hydroxybenzaldehyde (400 mg, 2.85 mmol), 3,4-dichlorobenzyl alcohol (665 mg, 3.76 mmol), and triphenylphosphine (980 mg, 3.74 mmol) were dissolved in tetrahydrofuran (8 mL), and a diethyl azodicarboxylate toluene solution (2.2 M, 1.71 mL, 3.76 mmol) was slowly added dropwise thereto at room temperature, and then, the resulting mixture was stirred under a nitrogen atmosphere at room temperature for 2 hours. The solvent in the reaction solution was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 95:5 (v/v)), whereby the objective title compound was obtained as a colorless oily substance (680 mg, yield: 80%).

Workup

  1. distillationThe solvent in the reaction solution was distilled off under reduced pressure
  2. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 95:5 (v/v)), whereby the objective title compound
  3. customwas obtained as a colorless oily substance (680 mg, yield: 80%)

Sources & evidence

ORD record
ord-4dd62a4d8538447393c32f3cbffb897c
Source dataset
uspto-grants-2012_07
Patent number
US08222281B2

Reaction notes

Loading…