Triphenylphosphine → 1-(2-Bromoethoxy)-4-phenoxybenzene

HRID 1669526Notes

Reaction equation

HRID 1669526 reaction equation
[O:1]([C:8]1[CH:17]=[CH:16][C:11]([O:12][CH2:13][CH2:14]O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:37]N1C(=O)CCC1=O>ClCCl>[Br:37][CH2:14][CH2:13][O:12][C:11]1[CH:16]=[CH:17][C:8]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 46767252-(4-Phenoxyphenoxy)ethanol

Product 1

HCID 132544871-(2-Bromoethoxy)-4-phenoxybenzeneYield 89.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(4-Phenoxy-phenoxy)-ethanol (2.2 g, 9.55 mmol), triphenylphosphine (2.76 g, 10.5 mmol), and dichloromethane (DCM) (36.7 mL) after stirring at 0° C., was added N-Bromosuccinimide (1.87 g, 10.5 mmol). The resulting mixture was stirred at 0° C. for 30 minutes and then at room temperature for 30 minutes. Reaction mixture was concentrated in vacuo to obtain the crude mixture, which was purified by of silica gel flash chromatography, using EtOAc/hexane (gradient system), to obtain the product (2.5 g, 89%): 1H NMR (400 MHz, CDCL3).

Workup

  1. waitat room temperature for 30 minutes
  2. customReaction mixture
  3. concentrationwas concentrated in vacuo
  4. customto obtain the crude mixture, which
  5. customwas purified by of silica gel flash chromatography

Sources & evidence

ORD record
ord-56f60ac58aeb4eeab51af21fdc1c878e
Source dataset
uspto-grants-2011_08
Patent number
US07989480B2

Reaction notes

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