4-Bromophenol → 2-(p-Bromophenoxy)ethanol

To a sol. of 4-bromophenol (40 g, 231 mmol) in EtOH (140 mL) was added NaOH (10.2 g, 254 mmol). The resulting mixture was stirred at 70° C. for 30 min until the whole amount of NaOH had dissolved. A sol. of 2-bromoethanol (17.3 mL, 231 mmol) in EtOH (40 mL) was added dropwise at 70° C. The sol. rapidly turned milky. The mixture was heated to reflux overnight. The solvents were removed under reduced pressure, and the residue was dissolved in EtOAc. The mixture was washed with water and brine, dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (EtOAc/heptane 1:5→1:4→1:3→1:2→EtOAc) yielded the title compound (39.2 g, 78%) as a pale brown oil that crystallized when placed at −18° C. Rf=0.3 in (EtOAc/heptane 1:1).

1. dissolutionhad dissolved
2. temperatureThe mixture was heated
3. temperatureto reflux overnight
4. customThe solvents were removed under reduced pressure
5. dissolutionthe residue was dissolved in EtOAc
6. washThe mixture was washed with water and brine
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. customthe solvents were removed under reduced pressure
10. customPurification of the crude by FC (EtOAc/heptane 1:5→1:4→1:3→1:2→EtOAc)

ORD record

ord-a82addf2ed6a48749deea4fc6c991f7a

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07915259B2