Triphenylphosphine → HCID 24694511, compound

HRID 2283111Notes

Reaction equation

HRID 2283111 reaction equation
[Br:1]N1C(=O)CCC1=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:28][O:29][C:30]1[CH:31]=[C:32]([CH2:36][O:37][CH2:38][CH2:39]O)[CH:33]=[CH:34][CH:35]=1>C(Cl)Cl.[Al]>[Br:1][CH2:39][CH2:38][O:37][CH2:36][C:32]1[CH:33]=[CH:34][CH:35]=[C:30]([O:29][CH3:28])[CH:31]=1

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 68461234HCID 68461234, compound

Product 1

HCID 24694511HCID 24694511, compoundYield 104.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent4×HCID 5359268AluminumSolvent

Procedure

A solution of N-bromosuccinimide (272 mg, 1.53 mmol) in DCM (2.5 mL) was added resin-bound triphenylphosphine (510 mg, 1.53 mEquiv, Fluka) in DCM (2.5 mL). The reaction was stirred at room temperature for 10 min. A solution of 2-({[3-(methyloxy)phenyl]methyl}oxy)ethanol (114 mg, 0.626 mmol) in DCM (1.5 mL) was added to the reaction, and the residual alcohol was transferred with additional DCM (1.5 mL). The reaction vessel was wrapped in aluminum foil and stirred at rt for 20 h. The reaction was filtered through a SPE cartridge (5 g silica) eluting with the following 10 mL fractions: DCM (fraction 1), 30% EtOAc/hexanes (fraction 2), and 50% EtOAc/hexanes (fraction 3) to give the title compound (160 mg). The product was characterized by 1H NMR (400 MHz) in CDCl3.

Workup

  1. stirringstirred at rt for 20 h
  2. filtrationThe reaction was filtered through a SPE cartridge (5 g silica)
  3. washeluting with the following 10 mL fractions

Sources & evidence

ORD record
ord-8cb9843415544144ae8b165834075c90
Source dataset
uspto-grants-2015_09
Patent number
US09144571B2

Reaction notes

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