Hydrochloric Acid → HCID 59729402, compound

HRID 1669230Notes

Reaction equation

HRID 1669230 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[CH:5]=[CH:6][C:7]=1[CH:8]=[CH:9][O:10]C.Cl.CCOC(C)=O.CCCCCC>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:19])([F:20])[F:21])=[CH:14][CH:13]=2)[CH:5]=[CH:6][C:7]=1[CH2:8][CH:9]=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226206Ethyl acetate hexaneHCID 67342613HCID 67342613, compound

Product 1

HCID 59729402HCID 59729402, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. solution of 3-fluoro-4-(2-methoxy-vinyl)-4′-trifluoromethyl-biphenyl (458 mg, 1.54 mmol) in THF (15 mL) is added dropwise concentrated hydrochloric acid (2.75 mL) and the reaction is warmed to room temperature. After 1 h TLC (30% EtOAc/hexane) indicates complete consumption of starting material. The reaction mixture was diluted with water and the pH is adjusted to 8 with solid NaHCO3. The reaction mixture is concentrated and the aqueous layer extracted with EtOAc (3×50 mL). The combined organic layers are washed with brine, dried (MgSO4), filtered, concentrated and chromatographed (40 g SiO2, 5% EtOAc/Hexanes) to yield the title compound (388 mg, 89%). 1NMR (400 MHz, CDCl3) δ ppm: 9.82 (s, 1H), 7.69 (q, 4H, J=8.4 Hz), 7.39 (dd, 1H, J=7.9, 1.3 Hz), 7.35 (dd, 1H, J=10.4, 1.5 Hz), 7.30 (t, 1H, J=7.7 Hz), 3.82 (s, 2H).

Workup

  1. customconsumption of starting material
  2. additionThe reaction mixture was diluted with water
  3. concentrationThe reaction mixture is concentrated
  4. extractionthe aqueous layer extracted with EtOAc (3×50 mL)
  5. washThe combined organic layers are washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customchromatographed (40 g SiO2, 5% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-c94755b972484086a4406922e9e89b75
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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