Triethyl phosphite → 2,3-Bis(diethoxyphosphoryl)-benzo[b]thiophene

HRID 969250Notes

Reaction equation

HRID 969250 reaction equation
[P:1]([O:8]CC)([O:5][CH2:6][CH3:7])[O:2][CH2:3][CH3:4].[CH:11]1[CH:16]=[C:15]2[C:17](Br)=[C:18](Br)[S:19][C:14]2=[CH:13][CH:12]=1>C(Cl)Cl.Cl[Pd]Cl>[CH2:3]([O:2][P:1]([C:18]1[S:19][C:14]2[CH:13]=[CH:12][CH:11]=[CH:16][C:15]=2[C:17]=1[P:1]([O:2][CH2:3][CH3:4])([O:5][CH2:6][CH3:7])=[O:8])([O:5][CH2:6][CH3:7])=[O:8])[CH3:4]

Participants

5

Reactant 2

HCID 31215Triethyl phosphiteHCID 949772,3-Dibromo-1-benzothiophene

Product 1

HCID 878300002,3-Bis(diethoxyphosphoryl)-benzo[b]thiopheneYield 60%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspension of PdCl2 (0.15 g) in 2,3-dibromothianaphthene (2.4 g) was brought to the temperature of 115° C., and P(OEt)3 (3.3 g) was then dropped under stirring and in an inert atmosphere. Once dropping was completed, the red solution was brought to 160° C. After 1 h 30 min, the mixture was diluted with CH2Cl2, washed twice with water and dehydrated. The solvent was evaporated at reduced pressure to yield a residue that underwent chromatography on silica gel by flash chromatography (AcOEt), to yield 2,3-bis(diethoxyphosphoryl)-benzo[b]thiophene (1.6 g) (yield 60%).

Workup

  1. additionwas then dropped
  2. customwas brought to 160° C
  3. washwashed twice with water
  4. customThe solvent was evaporated at reduced pressure
  5. customto yield a residue that underwent chromatography on silica gel by flash chromatography (AcOEt)

Sources & evidence

ORD record
ord-cbd6b1ef8bad466ca1449b9371fc67d1
Source dataset
uspto-grants-2007_12
Patent number
US07307037B2

Reaction notes

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