4-Fluorobenzonitrile → 4,4'-((1S,2S)-cyclohexane-1,2-dioxy)bisbenzonitrile

HRID 613791Notes

Reaction equation

HRID 613791 reaction equation
[H-].[Na+].[C@H:3]1([OH:10])[CH2:8][CH2:7][CH2:6][CH2:5][C@@H:4]1[OH:9].F[C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1.[OH-].[Na+]>CN(C=O)C.O>[C@H:3]1([O:10][C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=2)[CH2:8][CH2:7][CH2:6][CH2:5][C@@H:4]1[O:9][C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 145174-FluorobenzonitrileHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 70571101,2-Cyclohexanediol, (1S-trans)-

Product 1

HCID 675848624,4'-((1S,2S)-cyclohexane-1,2-dioxy)bisbenzonitrileYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (7.1 g, 0.3 mol) was dispersed in 200 ml DMF and added with (1S,2S)-cyclohexane-1,2-diol (11.42 g, 98.3 mmol) while cooling with ice. The mixture after being cooled with ice for another one hour was reacted at room temperature for 2 hours and cooled again, followed by addition of p-fluorobenzonitrile (25 g, 206 mmol). After the reaction was continued overnight, the mixture was added carefully with 5 ml water to inactivate excess sodium hydroxide, followed by distillation of DMF in pressure. The residue was added with 200 ml water and then extracted with ethyl acetate, followed by washing with a saturated solution of sodium chloride thereby obtaining a coarse crystalline product. The crystalline product was then recrystallized from 200 ml isopropanol thereby obtaining the intended product (26.2 g, 82.3 mmol, 84%).

Workup

  1. temperaturewhile cooling with ice
  2. temperatureThe mixture after being cooled with ice for another one hour
  3. customwas reacted at room temperature for 2 hours
  4. temperaturecooled again
  5. distillationfollowed by distillation of DMF in pressure
  6. additionThe residue was added with 200 ml water
  7. extractionextracted with ethyl acetate
  8. washby washing with a saturated solution of sodium chloride
  9. customthereby obtaining a coarse crystalline product
  10. customThe crystalline product was then recrystallized from 200 ml isopropanol

Sources & evidence

ORD record
ord-a82d338e69f846f2ac130487ed6ece12
Source dataset
uspto-grants-1999_12
Patent number
US06008401

Reaction notes

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