Sulfuric Acid → HCID 21908335, compound

HRID 1247576Notes

Reaction equation

HRID 1247576 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[F:9].[K].C[Si]([N-:15][Si](C)(C)C)(C)C.CCOCC.OS(O)(=O)=O.[C:30]1([CH3:36])[CH:35]=[CH:34]C=C[CH:31]=1>>[CH3:36][C:30]([C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[F:9])([CH2:35][CH3:34])[C:31]#[N:15].[CH3:36][C:30]([C:3]1[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=1[F:1])([CH2:35][CH3:34])[C:31]#[N:15]

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 1140TolueneHCID 3283Diethyl EtherHCID 151471,2,3-TrifluorobenzeneHCID 86585346HCID 86585346, compound

Product 2

HCID 21908335HCID 21908335, compoundHCID 21908343HCID 21908343, compound

Procedure

A solution of 5.0 g (37.85 mmol) of 1,2,3-trifluorobenzene, 3.30 g (39.74 mmol) of 2-methylbutylnitrile and 75.7 ml (0.5 M in toluene) of potassium-bis-trimethylsilylamide in 182 ml of toluene is heated for 3 hours at 60° C. It is mixed with ice water and ether. The organic phase is acidified with 10% H2SO4 and washed three times with water, dried (Na2SO4) and concentrated by evaporation in a vacuum. After chromatography on silica gel with 0–4% ether-hexane, 3.8 g of 2-methyl-2-(2,3-difluorophenyl)butyronitrile and 1.6 g of 2-methyl-2-(2,6-difluorophenyl)butyronitrile are obtained.

Workup

  1. washwashed three times with water
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-167bd1d102484d05a0afec28af9fd5bb
Source dataset
uspto-grants-2006_10
Patent number
US07129270B2

Reaction notes

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