Hydrochloric Acid → HCID 4070755, compound

HRID 2298530Notes

Reaction equation

HRID 2298530 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=1.C(N(CC)CC)C.[C:17](Cl)(=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19].Cl>C1COCC1>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19])=[C:4]([F:9])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 938984-Chloro-2-fluoroaniline

Product 1

HCID 4070755HCID 4070755, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred, cooled (0° C.) solution of 3.64 g (25.0 mmol) of 4-chloro-2-fluoroaniline and 4.2 mL (30 mmol) of triethylamine in 50 mL of THF was added 4.18 mL (26 mmol) of pivaloyl chloride. After stirring for 10 min. at 0° C. the mixture was warmed to ambient temperature and poured into 0.5N HCl. The mixture was extracted with 100 mL of ether, and the organic extract was washed sequentially with NaHCO3 and brine. The solution was dried (MgSO4), concentrated under reduced pressure, and chromatographed on silica gel (elution with 3:1 hexanes-ether) to give, after removal of solvent, 5.2 g (92%) of 4′-chloro-2′-fluoro-2,2-dimethylpropionanilide as a pale pink solid (IX), mp 70.5-71° C. 1H NMR (300 MHz, CDCl3) δ8.36(t, 1H, J=8.4 Hz); 7.57(br. s, 1H); 7.10-7.17(m, 2H); 1.30(s, 9H). 19F NMR (282 MHz, CDCl3) δ−129.8. High resolution mass spec: calculated for C11H14NOClF(M+H)+: 230.0748, found: 230.0760.

Workup

  1. temperaturewas warmed to ambient temperature
  2. extractionThe mixture was extracted with 100 mL of ether
  3. extractionthe organic extract
  4. washwas washed sequentially with NaHCO3 and brine
  5. dry with materialThe solution was dried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customchromatographed on silica gel (elution with 3:1 hexanes-ether)
  8. customto give
  9. customafter removal of solvent, 5.2 g (92%) of 4′-chloro-2′-fluoro-2,2-dimethylpropionanilide as a pale pink solid (IX), mp 70.5-71° C

Sources & evidence

ORD record
ord-607fd928598d4e6dad8a287afec46c22
Source dataset
uspto-grants-2002_12
Patent number
US06492515B2

Reaction notes

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