Triphenylphosphine → 1-{[(2-Bromoethyl)oxy]methyl}-4-(1,1-dimethylethyl)benzene

HRID 1875663Notes

Reaction equation

HRID 1875663 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]([C:32]1[CH:37]=[CH:36][C:35]([CH2:38][O:39][CH2:40][CH2:41]O)=[CH:34][CH:33]=1)([CH3:31])[CH3:30]>C(Cl)Cl.[Al]>[Br:1][CH2:41][CH2:40][O:39][CH2:38][C:35]1[CH:36]=[CH:37][C:32]([C:29]([CH3:31])([CH3:30])[CH3:28])=[CH:33][CH:34]=1

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 104885912-({[4-(1,1-Dimethylethyl)phenyl]methyl}oxy)ethanol

Product 1

HCID 136543781-{[(2-Bromoethyl)oxy]methyl}-4-(1,1-dimethylethyl)benzeneYield 12%

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-(1,1-dimethylethyl)phenyl]methyl}oxy)ethanol (160 mg, 0.768 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 (25 mg, 12%). 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-995770c1a637475189d090889b75f588
Source dataset
uspto-grants-2012_11
Patent number
US08309572B2

Reaction notes

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