Sodium hydride → 5-Bromo-2-[(oxan-4-yl)oxy]benzonitrile

HRID 2168155Notes

Reaction equation

HRID 2168155 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]1.[H-].[Na+].[Br:10][C:11]1[CH:12]=[CH:13][C:14](F)=[C:15]([CH:18]=1)[C:16]#[N:17]>CN(C=O)C>[Br:10][C:11]1[CH:12]=[CH:13][C:14]([O:7][CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)=[C:15]([CH:18]=1)[C:16]#[N:17]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74956Tetrahydro-4H-pyran-4-olHCID 27249005-Bromo-2-fluorobenzonitrile

Product 1

HCID 671146225-Bromo-2-[(oxan-4-yl)oxy]benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
45 °C

Procedure

To a solution of tetrahydro-pyran-4-ol (3.3 g, 33.0 mmol) in DMF (60 ml) at 0° C. is added sodium hydride (1.4 g, 33.0 mmol). 5-Bromo-2-fluoro-benzonitrile (5.5 g, 27.5 mmol) in DMF (30 ml) is added dropwise at 0° C. The reaction is stirred at 45° C. for 16 h. The reaction is cooled to room temperature and quenched by pouring the reaction into water (500 ml). The precipitate is filtered and dried under vacuum; yield: 6.8 g 5-bromo-2-(tetrahydro-pyran-4-yloxy)-benzonitrile; HPLC/MS: 2.27 min, [M+H]=283.

Workup

  1. temperatureThe reaction is cooled to room temperature
  2. customquenched
  3. additionby pouring
  4. customthe reaction into water (500 ml)
  5. filtrationThe precipitate is filtered
  6. customdried under vacuum
  7. custom2.27 min, [M+H]=283

Sources & evidence

ORD record
ord-d20e065ce78044c3b5cd9e75efd3fbfa
Source dataset
uspto-grants-2015_06
Patent number
US09045493B2

Reaction notes

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