Bis(2-bromoethyl) ether → 4-(4-bromophenyl)tetrahydro-2H-Pyran-4-carbonitrile

HRID 714877Notes

Reaction equation

HRID 714877 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].Br[CH2:18][CH2:19][O:20][CH2:21][CH2:22]Br>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:9]#[N:10])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 21521Bis(2-bromoethyl) etherHCID 27914Benzeneacetonitrile, 4-bromo-HCID 23665647Potassium tert-butoxide

Product 1

HCID 431190214-(4-bromophenyl)tetrahydro-2H-Pyran-4-carbonitrileYield 69.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-bromophenyl)acetonitrile (3.9 g) in tetrahydrofuran (50 mL) was added potassium t-butoxide (4.9 g) in an ice bath, and the mixture was stirred for 1 hr in an ice bath. 1-Bromo-2-(2-bromoethoxyl)ethane (5.8 g) was added thereto at the same temperature, and the mixture was stirred at room temperature for 10 hr. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (3.7 g).

Workup

  1. stirringat the same temperature, and the mixture was stirred at room temperature for 10 hr
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-6968c0db0fa243c0905adfa5d38bebf7
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

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