Triphenylphosphine → 1-(2-Bromo-ethoxymethyl)-4-chlorobenzene

HRID 1875669Notes

Reaction equation

HRID 1875669 reaction equation
[Br:1]N1C(=O)CCC1=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][O:36][CH2:37][CH2:38]O)=[CH:31][CH:30]=1>C(Cl)Cl.[Al]>[Br:1][CH2:38][CH2:37][O:36][CH2:35][C:32]1[CH:33]=[CH:34][C:29]([Cl:28])=[CH:30][CH:31]=1

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 27637512-[(4-Chlorobenzyl)oxy]-1-ethanol

Product 1

HCID 136543741-(2-Bromo-ethoxymethyl)-4-chlorobenzeneYield 57%

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 to resin-bound triphenylphosphine (510 mg, 1.53 mEquiv, Fluka) in DCM (2.5 mL), and the reaction was stirred at rt for 10 min. A solution of 2-{[(4-chlorophenyl)methyl]oxy}ethanol (129 mg, 0.691 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 vial was capped, 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 (98 mg, 57%). The product was characterized by 1H NMR (400 MHz) in CDCl3.

Workup

  1. customThe reaction vial was capped
  2. stirringstirred at rt for 20 h
  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-e32f015c2db34535bc1adb97ff92640d
Source dataset
uspto-grants-2012_11
Patent number
US08309572B2

Reaction notes

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