Phosphorus oxychloride → 6-Bromo-2-[4-(difluoromethyl)phenyl]benzo[d]oxazole

HRID 710103Notes

Reaction equation

HRID 710103 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=O)[C:10]2[CH:15]=[CH:14][C:13]([CH:16]([F:18])[F:17])=[CH:12][CH:11]=2)=[C:4]([OH:20])[CH:3]=1.P(Cl)(Cl)(Cl)=O>O1CCOCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]=[C:9]([C:10]3[CH:11]=[CH:12][C:13]([CH:16]([F:17])[F:18])=[CH:14][CH:15]=3)[O:20][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 71089555HCID 71089555, compound

Product 1

HCID 711144566-Bromo-2-[4-(difluoromethyl)phenyl]benzo[d]oxazoleYield 26.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

N-(4-Bromo-2-hydroxyphenyl)-4-(difluoromethyl)benzamide (0.5 g, 1.5 mmol) was dissolved in 1,4-Dioxane (10 ml) and added Phosphorus oxychloride (0.4 ml, 4.4 mmol). This mixture was refluxed for 2 h. 1,4-Dioxane removed on rotavapour to obtain the residue. Residue was washed with water to obtain solid. Solid was purified by column on 60-120 mesh silica gel using DCM as eluent to obtain the titled compound (130 mg) as an off-white solid. 1H-NMR (δ ppm, CDCl3, 400 MHz): 8.28 (d, J 8.4, 2H), 7.74 (d, J 1.7, 1H), 7.65-7.58 (m, 3H), 7.46 (dd, J 1.8, 8.4, 1H), 6.68 (t, J 56.2, 1H).

Workup

  1. temperatureThis mixture was refluxed for 2 h
  2. custom1,4-Dioxane removed on rotavapour
  3. customto obtain the residue
  4. washResidue was washed with water
  5. customto obtain solid
  6. customSolid was purified by column on 60-120 mesh silica gel

Sources & evidence

ORD record
ord-9b1de799ecfd48708d9462f11c018dd8
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

Loading…