Triethyl phosphite → HCID 15942001, compound

HRID 991980Notes

Reaction equation

HRID 991980 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Br:21])[C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([CH:18]([CH3:20])[CH3:19])[CH:12]=1)[CH2:5]Br.[P:22]([O:29]CC)([O:26][CH2:27][CH3:28])[O:23][CH2:24][CH3:25]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Br:21])[C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([CH:18]([CH3:20])[CH3:19])[CH:12]=1)[CH2:5][P:22](=[O:29])([O:26][CH2:27][CH3:28])[O:23][CH2:24][CH3:25]

Participants

4

Reactant 2

HCID 31215Triethyl phosphiteHCID 18415115HCID 18415115, compound

Product 1

HCID 15942001HCID 15942001, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3,5-dibromo-4-(4-hydroxy-3-isopropylphenoxy)benzylbromide (Example 13a) (491 mg, 1.03 mmol), triethyl phosphite (3.98 g, 12 mmol) in 20 ml of toluene was refluxed for 48 hours. The reaction mixture was concentrated and the residue was precipitated with a mixture of petroleum ether and EtOAc (8:2) to give 308 mg (0.577 mmol, 56%) of 3,5-dibromo-4-(4-hydroxy-3-isopropylphenoxy)benzyl phosphonic acid, diethyl ester as a white solid.

Workup

  1. temperaturewas refluxed for 48 hours
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was precipitated with a mixture of petroleum ether and EtOAc (8:2)

Sources & evidence

ORD record
ord-e5cfad3aef27453db229ced1b3bfbdef
Source dataset
uspto-grants-2002_10
Patent number
US06465687B1

Reaction notes

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