Triethylamine → 4-(Pyrrolidin-1-yl)-2,5-difluorobenzoic acid ethyl ester

HRID 10283Notes

Reaction equation

HRID 10283 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[C:5]1[CH:10]=[C:9]([F:11])[C:8](F)=[CH:7][C:6]=1[F:13])[CH3:2].[CH2:15]([N:17](CC)[CH2:18][CH3:19])[CH3:16].N1CCCC1>C(#N)C.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:14])[C:5]1[CH:10]=[C:9]([F:11])[C:8]([N:17]2[CH2:18][CH2:19][CH2:16][CH2:15]2)=[CH:7][C:6]=1[F:13])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31268PyrrolidineHCID 2774397Benzoic acid, 2,4,5-trifluoro-, ethyl ester

Product 1

HCID 210411804-(Pyrrolidin-1-yl)-2,5-difluorobenzoic acid ethyl esterYield 97%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2,4,5-trifluorobenzoic acid ethyl ester (Example 1e, 4.32 g, 21.2 mmol) in acetonitrile (25 mL) is added triethylamine (5.9 mL, 42.3 mmol) and pyrrolidine (2.2 mL, 25.4 mmol). After 24 hours, the reaction mixture is diluted with ethyl acetate and washed with saturated NaHCO3, water, and brine. The organic layer is dried over MgSO4, filtered, and the filtrate is concentrated to afford the title compound as an oil (5.25 g). MS CI: m/z 256 (MH+).

Workup

  1. washwashed with saturated NaHCO3, water, and brine
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-1240102ce85149d2a6f45262f5dded3b
Source dataset
uspto-grants-2006_08
Patent number
US07094780B1

Reaction notes

Loading…