1,3-Dibromopropane → 1-(4-Bromo-2-methoxyphenyl)cyclobutanecarbonitrile

HRID 1054850Notes

Reaction equation

HRID 1054850 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[C:4]([O:11][CH3:12])[CH:3]=1.Br[CH2:14][CH2:15][CH2:16]Br.[H-].[Na+]>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:9]#[N:10])[CH2:16][CH2:15][CH2:14]2)=[C:4]([O:11][CH3:12])[CH:3]=1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 24758Sodium hydrideHCID 52987748(4-Bromo-2-methoxyphenyl)acetonitrile

Product 1

HCID 866988391-(4-Bromo-2-methoxyphenyl)cyclobutanecarbonitrileYield 34.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring mixture of (4-bromo-2-methoxyphenyl)acetonitrile (904 mg, 4.00 mmol), 1,3-dibromo-propane (880 mg, 4.40 mmol) in dimethylformamide (10 mL) was added sodium hydride (352 mg, 8.80 mmol) at 0° C. After addition, the mixture was stirred at room temperature for 3 hours. The reaction mixture was quenched with water and extracted with dichloromethane (50 mL×3). The organic phases were combined, dried over sodium sulfate and concentrated in vacuo to give a brown solid. The solid was purification by combiflash chromatography (Petroleum ether/EtOAc=20:1 to 5:1) to give the title compound (370 mg, 34.8%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.10 (dd, 1H), 7.02 (d, 1H), 7.00 (d, 1H), 3.87 (s, 3H), 2.78 (m, 2H), 2.50 (m, 3H), 1.95 (m, 1H)

Workup

  1. additionAfter addition
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with dichloromethane (50 mL×3)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give a brown solid
  7. custompurification by combiflash chromatography (Petroleum ether/EtOAc=20:1 to 5:1)

Sources & evidence

ORD record
ord-7968ceb62ca74246b2fa8390dff949bb
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

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