Dichloromethane → HCID 118075456, compound

HRID 1051580Notes

Reaction equation

HRID 1051580 reaction equation
FC(F)(F)C(O)=O.[CH:8]1([O:12][C:13]2[CH:14]=[C:15]([F:28])[C:16]([F:27])=[C:17]([NH:19]C(=O)OC(C)(C)C)[CH:18]=2)[CH2:11][CH2:10][CH2:9]1.[Cl:29]CCl>>[ClH:29].[CH:8]1([O:12][C:13]2[CH:14]=[C:15]([F:28])[C:16]([F:27])=[C:17]([CH:18]=2)[NH2:19])[CH2:9][CH2:10][CH2:11]1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 118076294HCID 118076294, compound

Product 1

HCID 118075456HCID 118075456, compoundYield 89%

Procedure

Trifluoroacetic acid (70 mL) was added to a solution of tert-butyl 5-cyclobutoxy-2,3-difluorophenylcarbamate (32 g, 107 mmol) in dichloromethane (320 mL), and the resulting solution stirred overnight at room temperature. The reaction solution was concentrated, and the residue was dissolved in dichloromethane (500 mL). A solution of HCl (4 M in 1,4-dioxane, 120 mL) was slowly added with stirring. The resulting mixture was concentrated and poured into ethyl ether (480 mL). The resulting precipitate was filtered, and the filter cake was dried under reduced pressure to afford 5-cyclobutoxy-2,3-difluoroaniline hydrogen chloride (21 g, 89%) as a light yellow solid. MS (ESI, pos. ion) m/z 200 [M+H]+.

Workup

  1. concentrationThe reaction solution was concentrated
  2. dissolutionthe residue was dissolved in dichloromethane (500 mL)
  3. additionA solution of HCl (4 M in 1,4-dioxane, 120 mL) was slowly added
  4. stirringwith stirring
  5. concentrationThe resulting mixture was concentrated
  6. additionpoured into ethyl ether (480 mL)
  7. filtrationThe resulting precipitate was filtered
  8. customthe filter cake was dried under reduced pressure

Sources & evidence

ORD record
ord-427f00a84ac044508f1b3e42300ef34b
Source dataset
uspto-grants-2016_07
Patent number
US09388161B2

Reaction notes

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