1,2-Dibromoethane → 2-(2-Bromoethoxy)-4-nitrobenzonitrile

HRID 474240Notes

Reaction equation

HRID 474240 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C([O-])([O-])=O.[K+].[K+].[Br:19][CH2:20][CH2:21]Br>CC#N>[Br:19][CH2:20][CH2:21][O:1][C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 2861482-Hydroxy-4-nitrobenzonitrile

Product 1

HCID 666658762-(2-Bromoethoxy)-4-nitrobenzonitrileYield 49%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 2-hydroxy-4-nitro-benzonitrile (2 g, 12.19 mmol) and K2CO3 (3.36 g, 24.39 mmol) in MeCN (20 mL) was added 1,2-dibromoethane (3.4 g, 18.29 mmol) at room temperature. The reaction mixture was stirred at room temperature for 18 h while monitoring by TLC. The solvent was removed under reduced pressure and the residue was taken up in ethyl acetate (100 mL) and washed with brine (2×25 mL). The organic layer was dried over anhydrous sodium sulphate and concentrated to give 2-(2-bromoethoxy)-4-nitrobenzonitrile (1.6 g, 49%) as a light red solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.94-7.92 (1H, m), 7.82-7.78 (2H, m), 4.52 (2H, t, J=6.4 Hz), 3.73 (2H, t, J=6.4 Hz).

Workup

  1. customThe solvent was removed under reduced pressure
  2. washwashed with brine (2×25 mL)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6588d5cb481a47efa50446e19c23725d
Source dataset
uspto-grants-2014_01
Patent number
US08637523B2

Reaction notes

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