Bis(2-chloroethyl) ether → 4-(3-Fluorophenyl)oxane-4-carbonitrile

HRID 2078139Notes

Reaction equation

HRID 2078139 reaction equation
CC(C)([O-])C.[K+].[F:7][C:8]1[CH:9]=[C:10]([CH2:14][C:15]#[N:16])[CH:11]=[CH:12][CH:13]=1.Cl[CH2:18][CH2:19][O:20][CH2:21][CH2:22]Cl>CN(C=O)C>[F:7][C:8]1[CH:9]=[C:10]([C:14]2([C:15]#[N:16])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 8115Bis(2-chloroethyl) etherHCID 68145Benzeneacetonitrile, 3-fluoro-HCID 23665647Potassium tert-butoxide

Product 1

HCID 431190334-(3-Fluorophenyl)oxane-4-carbonitrileYield 165.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium tert-butoxide (5.48 g, 48.8 mmol) was added to a stirred solution of 2-(3-fluorophenyl)acetonitrile (2.58 mL, 22.2 mmol) in DMF (30 mL) at 0° C. under a nitrogen atmosphere. The mixture was stirred for 10 minutes at 0° C. before 1-chloro-2-(2-chloroethoxy)ethane (2.86 mL, 24.4 mmol) was added dropwise via syringe. The reaction mixture was allowed to warm to room temperature and stirred for 6 hours. The reaction mixture was then cooled to 0° C. and quenched with 10% HCl. The aqueous mixture was extracted with EtOAc (2×). The combined organic layers were washed with brine, dried (MgSO4), and concentrated in vacuo to give the product as an orange oil (7.53 g).

Workup

  1. additionwas added dropwise via syringe
  2. temperatureThe reaction mixture was then cooled to 0° C.
  3. customquenched with 10% HCl
  4. extractionThe aqueous mixture was extracted with EtOAc (2×)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f1a076987d2a4811bae528b42646e3e2
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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