Triethylamine → HCID 67444339, compound

HRID 1371939Notes

Reaction equation

HRID 1371939 reaction equation
[N+:1]([CH2:4][CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][C:15]([F:18])([F:17])[F:16])[CH:8]=1)O)([O-:3])=[O:2].CS(Cl)(=O)=O.C(N(CC)CC)C.C(OCC)(=O)C>ClCCl>[N+:1]([CH:4]=[CH:5][C:7]1[CH:8]=[C:9]([O:13][CH2:14][C:15]([F:16])([F:17])[F:18])[CH:10]=[CH:11][CH:12]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 67443319HCID 67443319, compound

Product 1

HCID 67444339HCID 67444339, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Combine 2-nitro-1-(3-trifluoroethoxyphenyl)ethanol (6.1 g, 24.2 mmol) and methanesulfonyl chloride (2.02 mL) in dichloromethane (50 mL) and cool in an ice-bath. Add dropwise, triethylamine (7.28 mL) while maintaining the temperature near 0° C. After 2 hours, pour into ethyl acetate, wash with water, dry with Na2SO4, filter, and then concentrate to residue. Chromatograph the residue on silica gel to give 3-(2-nitrovinyl)-1-trifluoroethoxybenzene: MS (MH+) 234; 1H NMR (CDCl3) 7.97 (1H, d, J=13.6 Hz), 7.57 (1H, d, J=13.6 Hz), 7.53–7.48 (2H, m), 7.40–7.35 (2H, m).

Workup

  1. additionAdd dropwise
  2. washwash with water
  3. dry with materialdry with Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate to residue

Sources & evidence

ORD record
ord-a07c53ae533f458bb6e6103cf6cf541c
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

Loading…