Triphenylphosphine → 1-(2-Bromoethoxymethyl)-4-fluorobenzene

HRID 2038318Notes

Reaction equation

HRID 2038318 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: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]([F:28])=[CH:30][CH:31]=1

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 12192386HCID 12192386, compound

Product 1

HCID 572052151-(2-Bromoethoxymethyl)-4-fluorobenzeneYield 48%

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-fluorophenyl)methyl]oxy}ethanol (122 mg, 0.717 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 (80 mg, 48%). 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-6e8357c1520b4731adc6f2899ffaf262
Source dataset
uspto-grants-2013_11
Patent number
US08575347B2

Reaction notes

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