Allyl bromide → Allyl-(2-iodo-4-trifluoromethyl-phenyl)-amine

HRID 2382088Notes

Reaction equation

HRID 2382088 reaction equation
[I:1][C:2]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[CH3:13][C:14]([O-])(C)[CH3:15].[K+].C1COCC1.C(Br)C=C>O>[CH2:15]([NH:4][C:3]1[CH:5]=[CH:6][C:7]([C:9]([F:10])([F:11])[F:12])=[CH:8][C:2]=1[I:1])[CH:14]=[CH2:13]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 8028TetrahydrofuranHCID 27833222-Iodo-4-(trifluoromethyl)anilineHCID 23665647Potassium tert-butoxide

Product 1

HCID 68555340Allyl-(2-iodo-4-trifluoromethyl-phenyl)-amineYield 33.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2-iodo-4-trifluoromethyl-aniline (5 g, 17.4 mmol), KOt-Bu (2.05 g, 18.3 mmol) and THF (200 mL) at −78° C., is added allyl bromide (2.21 g, 18.3 mmol). The resulting mixture is warmed to rt and stirred for 18 h. Water is added, and the mixture is extracted with EtOAc. The organic layer is separated, dried (Na2SO4), filtered and concentrated. The residue is chromatographed through silica gel eluting with 0-50% EtOAc in heptane to afford allyl-(2-iodo-4-trifluoromethyl-phenyl)-amine (1.9 g, 33%). MS 328 (M+H); 1H NMR (300 MHz, CDCl3): δ 7.90 (s, 1H), 7.45 (d, 1 H), 5.88-6.02 (m, 1H), 5.33 (d, 1 H), 5.25 (d, 1H), 4.72(broad s, 1H), 3.90 (s, 2H).

Workup

  1. extractionthe mixture is extracted with EtOAc
  2. customThe organic layer is separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is chromatographed through silica gel eluting with 0-50% EtOAc in heptane

Sources & evidence

ORD record
ord-6a2e71c1b9b941e8ab0246ec49293e3f
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

Loading…