2-Propylphenol → 4-Bromo-2-propylphenol

2-propylphenol (3.0 g, 0.022 mol) was dissolved in CHCl3 (100 mL) and magnetically stirred at room temperature. To this solution was added a solution of Tetrabutyl ammonium tribromide (10.68 g, 0.022 mol) in CHCl3 (100 mL). The resulting yellow solution was allowed to stir at room temperature for 1 hour. The reaction was quenched with a 5% solution of sodium thiosulfate (200 mL). The biphasic mixture was stirred for 15 min. The organics were separated and concentrated. The residue was dissolved in EtOAc (100 mL) and washed with water (2×100 mL) and brine (1×100 mL). The organics were dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography (silica gel) eluting with 3% EtOAc in Hexanes. The result was a yellow oil (4.54 g). 1H NMR (CDCl3): δ 1.00 (t, J=8.10 Hz, 3H), 1.52 (m, 2H), 2.50 (t, J=4.56 Hz, 2H), 4.95 (s, 1H), 6.72 (d, J=2.07 Hz 1H)), 6.80 (s, 1H), 6.85 (d, J=2.07 Hz, 1H).

1. stirringto stir at room temperature for 1 hour
2. customThe reaction was quenched with a 5% solution of sodium thiosulfate (200 mL)
3. stirringThe biphasic mixture was stirred for 15 min
4. customThe organics were separated
5. concentrationconcentrated
6. dissolutionThe residue was dissolved in EtOAc (100 mL)
7. washwashed with water (2×100 mL) and brine (1×100 mL)
8. dry with materialThe organics were dried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated
11. customThe residue was purified by flash chromatography (silica gel)
12. washeluting with 3% EtOAc in Hexanes

ORD record

ord-bee6b274d0f04c67a11a778ea3fc3a67

Source dataset

uspto-grants-2009_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07473790B2