Trifluoroacetic acid → 4-(3-Bromo-4-methoxyphenoxy)-3,5-dimethylnitrobenzene

HRID 584036Notes

Reaction equation

HRID 584036 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N+:18]([O-:20])=[O:19])[CH:5]=[C:6]([CH3:17])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1.[Br:21]N1C(=O)CCC1=O.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[Br:21][C:13]1[CH:14]=[C:9]([CH:10]=[CH:11][C:12]=1[O:15][CH3:16])[O:8][C:7]1[C:6]([CH3:17])=[CH:5][C:4]([N+:18]([O-:20])=[O:19])=[CH:3][C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 67184N-bromobutanimide2×HCID 100846724-(4-Methoxy-phenoxy)-3,5-dimethyl-nitrobenzene

Product 1

HCID 223397284-(3-Bromo-4-methoxyphenoxy)-3,5-dimethylnitrobenzeneYield 97.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 3,5-dimethyl-4-(4′-methoxyphenoxy)nitrobenzene (4.0 g) (J. Med. Chem., 38: 703 (1995)) in chloroform (150 ml) were added N-bromosuccinimide (2.6 g) and trifluoroacetic acid (1.1 ml), and the resulting mixture was heated under reflux for 90 min. Additional portions of N-bromosuccinimide (2.6 g) and trifluoroacetic acid (1.1 ml) were added, followed by further heating for 18 h. The reaction was washed with sodium bicarbonate, dried (Na2SO4) and concentrated to afford the title compound of Step A as an orange solid (5.0 g). MS (APCl+) Calc: 351; Found: 352 (M+1).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 90 min
  3. temperatureby further heating for 18 h
  4. washThe reaction was washed with sodium bicarbonate
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-81eff7552324478280227e4b33a50a8d
Source dataset
uspto-grants-2005_08
Patent number
US06924310B2

Reaction notes

Loading…