Hydrochloric Acid → Ethyl 2-(4-cyano-2-fluorophenyl)acetate

HRID 526424Notes

Reaction equation

HRID 526424 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12][C:13](C)(C)[CH3:14])=[O:11])=[C:5]([F:17])[CH:4]=1)#[N:2].Cl.O1CCOCC1>CCO>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:5]([F:17])[CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 312751,4-Dioxane2×HCID 117601243Tert-butyl 2-(4-cyano-2-fluorophenyl)acetate

Product 1

HCID 117601416Ethyl 2-(4-cyano-2-fluorophenyl)acetateYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Combined tert-butyl 2-(4-cyano-2-fluorophenyl)acetate (227.3 mg, 0.966 mmol) with EtOH (5 mL) and added a 4M hydrogen chloride solution in dioxane (0.121 mL, 0.483 mmol) and stirred in a heating block at 60° C. for 16 h. Then the reaction mixture was concentrated via rotary evaporation and re-constituted in EtOH (5 mL). An additional portion of a 4M hydrogen chloride solution in dioxane (17.61 mg, 0.483 mmol) was added to the vial and the mixture was stirred at 60° C. for an additional 1 h. The reaction mixture was then concentrated via rotary evaporation and dried in vacuo to give the title compound (198 mg, 99% yield) as a yellow oil. 1H NMR (400 MHz, chloroform-d) δ ppm 1.27 (t, J=7.07 Hz, 3H) 3.72 (d, J=1.26 Hz, 2H) 4.19 (q, J=7.24 Hz, 2H) 7.36-7.40 (m, 1H) 7.40-7.43 (m, 1H) 7.43-7.46 (m, 1H). MS m/z [M+H]+ 208.0.

Workup

  1. concentrationThen the reaction mixture was concentrated via rotary evaporation and re-constituted in EtOH (5 mL)
  2. stirringwas stirred at 60° C. for an additional 1 h
  3. concentrationThe reaction mixture was then concentrated via rotary evaporation
  4. customdried in vacuo

Sources & evidence

ORD record
ord-d287b526c9644a14978510eb190ed768
Source dataset
uspto-grants-2016_05
Patent number
US09345713B2

Reaction notes

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