Benzyl Bromide → HCID 21976855, compound

4-(3-Hydroxy-propylsulfanyl)-phenol (CAB02029, 3.686 g, 20 mmol) was dissolved in ethanol (50 mL) and potassium tert-Butoxide (2.80 g, 25 mmol) and benzyl bromide (3.0 mL, ca. 25 mmol) were added. The mixture was stirred overnight at room temperature, the precipitated potassium bromide was filtered off and the filtrate was concentrated under reduced pressure. The resulting yellow solid was dissolved in ethyl acetate (1.00 mL), the solution was washed with water (100 mL) and brine (100 mL), dried over sodium sulphate and concentrated under reduced pressure. The residue was dissolved in dichloromethane (ca. 10 mL) and the product was precipitated by addition of hexane (ca. 200 mL). The crystalline product was collected and dried under high vacuum. Yield: 4.481 g (82%) colourless, small plates. 1H-NMR (400 MHz, CDCl3) δ=1.45 (br s, 1H, —OH), 1.82-1.87 (m, 2H), 2.84 (t, J=7.4 Hz, 2H), 3.74-3.78 (m, 2H), 5.05 (s, 2H, —OCH2Ph), 6.90-6.93 (m, 2H, 7.31-7.44 (m, 7H).

1. filtrationthe precipitated potassium bromide was filtered off
2. concentrationthe filtrate was concentrated under reduced pressure
3. dissolutionThe resulting yellow solid was dissolved in ethyl acetate (1.00 mL)
4. washthe solution was washed with water (100 mL) and brine (100 mL)
5. dry with materialdried over sodium sulphate
6. concentrationconcentrated under reduced pressure
7. dissolutionThe residue was dissolved in dichloromethane (ca. 10 mL)
8. customthe product was precipitated by addition of hexane (ca. 200 mL)
9. customThe crystalline product was collected
10. customdried under high vacuum

ORD record

ord-b2a4954f3f2b4010ac9be43a08f929da

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07745472B2