Hydrochloric Acid → HCID 25158671, compound

HRID 1874777Notes

Reaction equation

HRID 1874777 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([OH:10])[CH:9]=1)[C:5]#[N:6].[H-].[Na+].F[C:14]1[C:19]([F:20])=[C:18]([F:21])[CH:17]=[CH:16][C:15]=1[N+:22]([O-:24])=[O:23].Cl>C1COCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:14]2[C:15]([N+:22]([O-:24])=[O:23])=[CH:16][CH:17]=[C:18]([F:21])[C:19]=2[F:20])[CH:9]=1)[C:5]#[N:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 698711,2,3-Trifluoro-4-nitrobenzeneHCID 219498783-Chloro-5-hydroxybenzonitrile

Product 1

HCID 25158671HCID 25158671, compoundYield 74.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

3-Chloro-5-hydroxybenzonitrile (20.0 g, 130 mmol) was dissolved in anhydrous THF (500 mL) and cooled to 0° C. Sodium hydride (60% dispersion in oil, 4.81 g, 125 mmol) was added and stirred for 30 minutes. 2,3,4-Trifluoronitrobenzene (23.06 g, 130 mmol) was added and the reaction was allowed to warm to RT. Stirring was continued until TLC showed no remaining starting material. The reaction mixture was poured into a mixture of 10% HCl and ice. Ethyl acetate was added and the organic layer was separated, dried over MgSO4, filtered and evaporated. The resulting oil was triturated with hexanes and Et2O to afford a solid. The washing were collected, evaporated and triturated with hexanes. The materials were combined to afford the title compound (30 g, 74%) as a solid. 1H NMR (400 MHz, CDCl3): δ ppm 7.98 (ddd, 1H), 7.43 (t, 1H), 7.34 (ddd, 1H), 7.21 (t, 1H), 7.08 (dd, 1H).

Workup

  1. temperatureto warm to RT
  2. stirringStirring
  3. customthe organic layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe resulting oil was triturated with hexanes and Et2O
  8. customto afford a solid
  9. customThe washing were collected
  10. customevaporated
  11. customtriturated with hexanes

Sources & evidence

ORD record
ord-6bf55c538e60475eaf765cd0fe044d1e
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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