4-Fluoro-3-nitrobenzotrifluoride → HCID 67520356, compound

HRID 1925404Notes

Reaction equation

HRID 1925404 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[CH3:15][N:16]([CH3:22])[C@@H:17]1[CH2:21][CH2:20][NH:19][CH2:18]1.C([O-])(O)=O.[Na+]>C1COCC1>[N+:12]([C:3]1[CH:4]=[C:5]([C:8]([F:11])([F:10])[F:9])[CH:6]=[CH:7][C:2]=1[N:19]1[CH2:20][CH2:21][C@@H:17]([N:16]([CH3:22])[CH3:15])[CH2:18]1)([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 677784-Fluoro-3-nitrobenzotrifluorideHCID 516892Sodium BicarbonateHCID 2758521(3R)-(+)-3-(Dimethylamino)pyrrolidine

Product 1

HCID 67520356HCID 67520356, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-fluoro-2-nitro-4-(trifluoromethyl)benzene (0.67 mL, 4.78 mmol) in THF (25 mL) was added (R)-N,N-dimethylpyrrolidin-3-amine (0.66 g, 5.74 mmol) and NaHCO3 (1.1 g, 13.15 mmol). The reaction was stirred at RT and monitored by LCMS for disappearance of starting material and formation of product. The mixture was concentrated, diluted with CH2Cl2, washed with H2O and then brine. Drying with MgSO4 was followed by filtration and concentration to afford the product as an orange oil.

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with CH2Cl2
  3. washwashed with H2O
  4. dry with materialDrying with MgSO4
  5. filtrationwas followed by filtration and concentration

Sources & evidence

ORD record
ord-62f1b3dbbc3b40b1aa5b7c4438c1824b
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

Loading…