(Diethylamino)sulfur trifluoride → HCID 68701047, compound

HRID 2092502Notes

Reaction equation

HRID 2092502 reaction equation
O[C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[CH:7]=1)([CH3:5])[C:3]#[N:4].C(N(S(F)(F)[F:21])CC)C>C(Cl)Cl>[F:21][C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[CH:7]=1)([CH3:5])[C:3]#[N:4]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 83855071HCID 83855071, compound

Product 1

HCID 68701047HCID 68701047, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled solution (T=−60° C.) of 2-hydroxy-2-(3-nitrophenyl)propanenitrile (1.11 g, 5.8 mmol) in dry CH2Cl2 (60 ml), (diethylamino)sulfur trifluoride (0.8 mL, 6.0 mmol) was added under vigorous stirring. The resulting reaction mixture was left stirring at room temperature overnight. The reaction mixture was diluted with a buffer solution (pH=5.0) (10 ml), trasferred into a separator funnel and the two phases were debated and separated. The aqueous one was extracted with water (3×10 mL); the collected organic extracts were dried over Na2SO4 and evaporated under vacuum to give a crude which was purified by flash chromatography to afford pure 2-fluoro-2-(3-nitrophenyl)propanenitrile (0.9 g, yield 79%) as brown oil. 1H-NMR (CDCl3) δ 8.52 (s, 1H), 8.45 (d, 1H, J=3 Hz), 7.90 (m, 1H), 7.70 (t, 1H, J=7 Hz), 2.12 (d, 3H, J=23 Hz).

Workup

  1. customThe resulting reaction mixture
  2. waitwas left
  3. customtrasferred into a separator funnel
  4. customseparated
  5. extractionThe aqueous one was extracted with water (3×10 mL)
  6. dry with materialthe collected organic extracts were dried over Na2SO4
  7. customevaporated under vacuum
  8. customto give a crude which
  9. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-35345a8b6b4b4fea9a02140d06d0b906
Source dataset
uspto-grants-2013_05
Patent number
US08440711B2

Reaction notes

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