Sodium Hydroxide → (E)-3-(3-Bromo-4-fluorophenyl)acrylonitrile

HRID 474553Notes

Reaction equation

HRID 474553 reaction equation
[Br-].[C:2]([CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)#[N:3].[OH-].[Na+].[Br:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][C:34]=1[F:35])[CH:30]=O>C(Cl)Cl.O>[Br:26][C:27]1[CH:28]=[C:29](/[CH:30]=[CH:4]/[C:2]#[N:3])[CH:32]=[CH:33][C:34]=1[F:35]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 1736043-Bromo-4-fluorobenzaldehydeHCID 11811037(Cyanomethyl)triphenylphosphonium bromide

Product 1

HCID 61702072(E)-3-(3-Bromo-4-fluorophenyl)acrylonitrileYield 125.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of (cyanomethyl)triphenylphosphonium bromide (70.6 g, 185 mmol) and sodium hydroxide (7.39 g, 185 mmol) in DCM (100 mL) and water (300.00 mL) at 0° C. was added 3-bromo-4-fluorobenzaldehyde (25.0 g, 123 mmol). It was allowed to warm to room temperature and stirred for 2 h. The organic layer was separated, and the water layer was extracted with DCM twice. The combined organic phases were dried over Na2SO4 and concentrated to give a crude product, which was washed with diethyl ether. The residue was purified to give the title compound as a white solid (35 g, 88% yield). LCMS: rt=1.50 min, [M+H+]=226

Workup

  1. customThe organic layer was separated
  2. extractionthe water layer was extracted with DCM twice
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. concentrationconcentrated
  5. customto give a crude product, which
  6. washwas washed with diethyl ether
  7. customThe residue was purified

Sources & evidence

ORD record
ord-99c933f36cb64fdb8139b594bd3d64b7
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

Loading…