Phosphorus oxybromide → HCID 18511456, compound

HRID 1370345Notes

Reaction equation

HRID 1370345 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[C:12]([CH3:13])=[C:11](O)[C:10]2[C:5](=[C:6]([C:15]([F:18])([F:17])[F:16])[CH:7]=[CH:8][CH:9]=2)[N:4]=1.P(Br)(Br)([Br:23])=O>C1(C)C=CC=CC=1>[F:1][C:2]([F:20])([F:19])[C:3]1[C:12]([CH3:13])=[C:11]([Br:23])[C:10]2[C:5](=[C:6]([C:15]([F:18])([F:17])[F:16])[CH:7]=[CH:8][CH:9]=2)[N:4]=1

Participants

4

Reactant 2

HCID 24613Phosphorus oxybromideHCID 178427870HCID 178427870, compound

Product 1

HCID 18511456HCID 18511456, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2,8-bis(trifluoromethyl)-3-methyl-4-quinolinol (5.9 g, 20 mmol) in toluene (20 mL) was treated with POBr3 (6.0 g, 21 mmol), heated to reflux for 30 min, cooled in ice, quenched with water and extracted with EtOAc (2×50 mL). The combined extracts were dried (MgSO4), concentrated in vacuo and the resulting brown solid purified by flash chromatography [SiO2; heptane] to give the product (5.8 g, 81%) as a white crystalline solid: mp 81.9-82.3° C.; IR νmax (Nujol)/cm−1 2955, 2924, 2854, 1574, 1465, 1364, 1299, 1281, 1213, 1189, 1141; NMR δH (400 MHz, CDCl3) 2.77 (3H, s), 7.78 (1H, t, J 8.1 Hz), 8.14 (1H, d, 7.4 Hz), 8.49 (1H, d, J 8.5 Hz).

Workup

  1. temperatureheated
  2. temperatureto reflux for 30 min
  3. temperaturecooled in ice
  4. customquenched with water
  5. extractionextracted with EtOAc (2×50 mL)
  6. dry with materialThe combined extracts were dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customthe resulting brown solid purified by flash chromatography [SiO2; heptane]

Sources & evidence

ORD record
ord-085cc5e229cb408ca2d72c87d34384a9
Source dataset
uspto-grants-2003_06
Patent number
US06583156B1

Reaction notes

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