Bis(2-bromoethyl) ether → HCID 117667857, compound

HRID 712760Notes

Reaction equation

HRID 712760 reaction equation
[H-].[Na+].C(=O)=O.CO.[Br:8][C:9]1[CH:10]=[C:11]([CH2:15][C:16]#[N:17])[CH:12]=[N:13][CH:14]=1.Br[CH2:19][CH2:20][O:21][CH2:22][CH2:23]Br>C1COCC1>[Br:8][C:9]1[CH:10]=[C:11]([C:15]2([C:16]#[N:17])[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[CH:12]=[N:13][CH:14]=1

Participants

6

Reactant 4

HCID 21521Bis(2-bromoethyl) etherHCID 24758Sodium hydrideHCID 150054172-(5-Bromopyridin-3-yl)acetonitrileHCID 21973728Carbon dioxide methanol

Product 1

HCID 117667857HCID 117667857, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under argon, NaH (60% in mineral oil, 0.497 g, 12.4 mmol) is added into THF (10 mL). The reaction mixture is cooled on a bath of dry ice/CH3OH. A solution of (5-bromo-pyridin-3-yl)-acetonitrile (1.0 g, 5.0 mmol) and 2-bromoethyl ether (0.719 mL, 5.15 mmol) in THF (4.5 mL) is added dropwise. The reaction is stirred for 30 min. The dry ice/MeOH bath is removed and the mixture is stirred at room temperature for 14 hrs. The reaction is quenched by slow addition of MeOH (5 mL). The mixture is then concentrated. The resulting crude product is purified by normal phase chromatography using 0-3% MeOH in DCM as the gradient to afford 4-(5-bromo-pyridin-3-yl)-tetrahydro-pyran-4-carbonitrile (1.07 g, 79% yield).

Workup

  1. customThe dry ice/MeOH bath is removed
  2. stirringthe mixture is stirred at room temperature for 14 hrs
  3. customThe reaction is quenched by slow addition of MeOH (5 mL)
  4. concentrationThe mixture is then concentrated
  5. customThe resulting crude product is purified by normal phase chromatography

Sources & evidence

ORD record
ord-b56097f9fe374a4bb0c850cb1ba1c396
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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