Bis(2-bromoethyl) ether → HCID 67099951, compound

HRID 2078361Notes

Reaction equation

HRID 2078361 reaction equation
[H-].[Na+].Br[CH2:4][CH2:5][O:6][CH2:7][CH2:8]Br.[F:10][C:11]1[C:16]([F:17])=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:18][C:19]#[N:20]>CN1C(=O)CCC1.CCOCC>[F:10][C:11]1[C:16]([F:17])=[CH:15][CH:14]=[CH:13][C:12]=1[C:18]1([C:19]#[N:20])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1

Participants

6

Reactant 3

HCID 21521Bis(2-bromoethyl) etherHCID 24758Sodium hydrideHCID 5189682,3-Difluorophenylacetonitrile

Product 1

HCID 67099951HCID 67099951, compoundYield 73.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of sodium hydride (2 mL, 88 mmol) in 120 mL NMP was stirred at 0° C. and treated with a mixture of bis(2-bromoethyl)ether (9 mL, 40 mmol) and 2-(2,3-difluorophenyl)acetonitrile (6.12 g, 40 mmol) in 20 mL ether. The reaction was stirred at room temperature for 4 hours, carefully quenched with 20 mL H2O, and neutralized to pH=5 with concentrated HCl. The mixture was further diluted with 200 mL water, and the precipitate was collected by filtration. The solid was redissolved in 200 mL ether, washed with 20 mL saturated NaCl, dried over anhydrous Na2SO4, and concentrated to give 6.55 g of the title compound as a white solid. MS m/e: (M+H)+ 224.

Workup

  1. stirringThe reaction was stirred at room temperature for 4 hours
  2. customcarefully quenched with 20 mL H2O
  3. additionThe mixture was further diluted with 200 mL water
  4. filtrationthe precipitate was collected by filtration
  5. dissolutionThe solid was redissolved in 200 mL ether
  6. washwashed with 20 mL saturated NaCl
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-141e5c2c9ada4b739607e4c1bd8e0510
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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