Sodium Chloride → HCID 54213593, compound

HRID 1395613Notes

Reaction equation

HRID 1395613 reaction equation
[F:1][C:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[CH:3][CH3:4].Br[N:12]1C(=O)CC[C:13]1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Na+].[Cl-].[C-]#N.[Na+]>C(Cl)(Cl)(Cl)Cl.CN(P(N(C)C)(N(C)C)=O)C.O.CCOCC.CCCCCC.CCCCCC>[F:1][C:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[CH:3][CH2:4][C:13]#[N:12]

Participants

11

Reactant 5

HCID 5234Sodium ChlorideHCID 7187Benzoyl PeroxideHCID 8929Sodium CyanideHCID 67184N-bromobutanimideHCID 53826094HCID 53826094, compound

Product 1

HCID 54213593HCID 54213593, compound

Reagents, catalysts & solvents 5

HCID 962WaterSolvent2×HCID 5943Carbon TetrachlorideSolventHCID 8058HexaneSolvent2×HCID 12679HexamethylphosphoramideSolventHCID 21584099Diethylether hexaneSolvent

Procedure

To 1.36 g (10 mmol) of α-fluoro-β-methylstyrene in 20 ml of CCl4 is added 1.78 g (10 mmol) of N-bromosuccinimide and 50 g of dibenzoyl peroxide. The reaction is stirred overnight and then poured into hexane and water. The hexane layer is shaken against sat. NaCl solution and dried (Na2SO4). The product bromide after solvent removal is dissolved in 10 ml of THF and 10 ml of HMPT, and 1.96 g (40 mmol) of sodium cyanide is added. The reaction is warmed to 60° and after 24 hours poured into ether/hexane (2:8) and water. The organic phase is washed several times with water, dried, and solvent removed to give 4-fluoro-4-phenyl-3-butenonitrile.

Workup

  1. dry with materialdried (Na2SO4)
  2. customThe product bromide after solvent removal
  3. dissolutionis dissolved in 10 ml of THF
  4. temperatureThe reaction is warmed to 60° and after 24 hours
  5. washThe organic phase is washed several times with water
  6. customdried
  7. customsolvent removed

Sources & evidence

ORD record
ord-f8e2eb2da1234eec97c47021030f7bea
Source dataset
uspto-grants-1980_05
Patent number
US04204071

Reaction notes

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