Phosphorus tribromide → 6-(1-Bromoethyl)-quinoline

HRID 897220Notes

Reaction equation

HRID 897220 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([CH:11](O)[CH3:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.P(Br)(Br)[Br:15].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:15][CH:11]([C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:1]=[CH:2][CH:3]=[CH:4]2)[CH3:12]

Participants

5

Reactant 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 223480131-(Quinolin-6-yl)ethanol

Product 1

HCID 223480496-(1-Bromoethyl)-quinolineYield 73.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-quinolin-6-yl-ethanol (0.4 g, 2.3 mmol) in dry CH2Cl2 (20 mL) was added PBr3 (0.22 mL, 2.3 mmol). The reaction mixture was allowed to stir at room temperature for 12 h, and then was treated slowly with a saturated solution of NaHCO3 (100 mL) until basic. The CH2Cl2 layer was removed, product was extracted from the aqueous layer with ethyl acetate (100 mL), and the combined organic layers were dried over MgSO4, filtered and concentrated in vacuo to afford 0.4 g (72%) of a pale yellow oil. 1H NMR (300 MHz, CDCl3) δ ppm 8.89-8.96 (m, 1H), 8.11-8.20 (m, 2H), 7.82-7.89 (m, 2H), 7.41-7.49 (m, 1H), 5.39 (dt, 1H), 2.15 (d, 3H).

Workup

  1. customThe CH2Cl2 layer was removed
  2. extractionproduct was extracted from the aqueous layer with ethyl acetate (100 mL)
  3. dry with materialthe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-392e89fb27514e5695b45e86b207357b
Source dataset
uspto-grants-2005_07
Patent number
US06921821B2

Reaction notes

Loading…