Dichloromethane → 1-(2-chloroethyl)-4-nitrobenzene

HRID 1777769Notes

Reaction equation

HRID 1777769 reaction equation
N1[C:8]([Cl:9])=NC(Cl)=NC=1Cl.C(Cl)Cl.[N+:13]([C:16]1[CH:24]=[CH:23][C:19]([CH2:20]CO)=[CH:18][CH:17]=1)([O-:15])=[O:14]>CN(C=O)C.C([O-])([O-])=O.[Na+].[Na+]>[Cl:9][CH2:8][CH2:20][C:19]1[CH:23]=[CH:24][C:16]([N+:13]([O-:15])=[O:14])=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 74944-Nitrophenethyl alcoholHCID 7954Cyanuric chloride

Product 1

HCID 2858461-(2-chloroethyl)-4-nitrobenzene

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 10340Sodium CarbonateSolvent

Procedure

A solution of cyanuric chloride (1.83 g) in DMF (2 mL) was stirred at RT for 1 h. To the resulting white suspension was added DCM (25 mL) followed by 4-nitrophenethyl alcohol (1.59 g). The reaction mixture was stirred at RT for 4 h and diluted with 1M Na2CO3. The phases were separated, the org. layer was washed with 1M HCl and brine and evaporated in vacuo to afford 1.4 g of orange slurry. 1H-NMR (CDCl3): 8.22 (m, 2H); 7.43 (m, 2H); 3.79 (t, 2H, 7.0 Hz); 3.20 (t, 2H, 6.8 Hz).

Workup

  1. customThe phases were separated
  2. washlayer was washed with 1M HCl and brine
  3. customevaporated in vacuo
  4. customto afford 1.4 g of orange slurry

Sources & evidence

ORD record
ord-b8570262b724416aa233fc459b968525
Source dataset
uspto-grants-2016_02
Patent number
US09266876B2

Reaction notes

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