Triphenylphosphine → HCID 13654385, compound

HRID 2283128Notes

Reaction equation

HRID 2283128 reaction equation
[Br:1]N1C(=O)CCC1=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:28][C:29]1[CH:30]=[C:31]([CH2:35][O:36][CH2:37][CH2:38]O)[CH:32]=[CH:33][CH:34]=1>C(Cl)Cl.[Al]>[Br:1][CH2:38][CH2:37][O:36][CH2:35][C:31]1[CH:32]=[CH:33][CH:34]=[C:29]([F:28])[CH:30]=1

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 23325086851859-50-2

Product 1

HCID 13654385HCID 13654385, compoundYield 78.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 5359268AluminumSolvent

Procedure

N-bromosuccinimide (146 mg, 0.820 mmol) was added to resin-bound triphenylphosphine (274 mg, 0.822 mEquiv, Fluka) and 2-{[(3-fluorophenyl)methyl]oxy}ethanol (70 mg, 0.411 mmol) in DCM (4 mL). The reaction vial was sealed with a Teflon-lined cap, wrapped in aluminum foil, and shaken at rt for 17 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 (75 mg, 78%). The product was characterized by 1H NMR (400 MHz) in CDCl3.

Workup

  1. customThe reaction
  2. customlined cap
  3. filtrationThe reaction was filtered through a SPE cartridge (5 g silica)
  4. washeluting with the following 10 mL fractions

Sources & evidence

ORD record
ord-edaa570c0bfe409db161bcd0672dd0e5
Source dataset
uspto-grants-2015_09
Patent number
US09144571B2

Reaction notes

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