Triphenylphosphine → HCID 68959932, compound

HRID 533883Notes

Reaction equation

HRID 533883 reaction equation
[Br:1]N1C(=O)CCC1=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:28][C:29]([O:37][CH2:38][CH2:39]O)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH3:30]>C(Cl)Cl.[Al]>[Br:1][CH2:39][CH2:38][O:37][C:29]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([CH3:30])[CH3:28]

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 68960487HCID 68960487, compound

Product 1

HCID 68959932HCID 68959932, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 5359268AluminumSolvent

Procedure

N-bromosuccinimide (119 mg, 0.666 mmol) was added to resin-bound triphenylphosphine (222 mg, 0.666 mEquiv, Fluka) and 2-[(1-methyl-1-phenylethyl)oxy]ethanol (60 mg, 0.333 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 (34 mg, 42%). 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-9284da7040e44250a6670003f04b7603
Source dataset
uspto-grants-2014_10
Patent number
US08853404B2

Reaction notes

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