2-Bromoethanol → HCID 68379812, compound

A mixture of 4-fluoro-2-(trifluoromethyl)phenol (1.05 g, 5.83 mmol), 2-bromoethanol (0.62 mL, 8.7 mmol) and triphenylphosphine (2.29 g, 8.73 mmol) in tetrahydrofuran (20 mL) was stirred for 5 minutes. Diisopropyl azodicarboxylate (94%, 1.84 mL, 8.71 mmol) was then added drop-wise over 20 minutes, and the reaction was stirred at room temperature for 16 hours. Water (50 mL) was added, and the mixture was extracted with dichloromethane (2×75 mL). The combined organic layers were washed with saturated aqueous sodium chloride solution (50 mL), dried over magnesium sulfate, and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 0% to 10% ethyl acetate in heptane) afforded the title compound as a white solid. Yield: 600 mg, 2.09 mmol, 36%. GCMS m/z 286. 1H NMR (400 MHz, CDCl3) δ 3.66 (dd, J=6.6, 6.4 Hz, 2H), 4.35 (dd, J=6.5, 6.4 Hz, 2H), 6.97 (br dd, J=9.0, 4.1 Hz, 1H), 7.18-7.24 (m, 1H), 7.32 (br dd, J=8.3, 3.2 Hz, 1H).

1. stirringthe reaction was stirred at room temperature for 16 hours
2. extractionthe mixture was extracted with dichloromethane (2×75 mL)
3. washThe combined organic layers were washed with saturated aqueous sodium chloride solution (50 mL)
4. dry with materialdried over magnesium sulfate
5. concentrationconcentrated in vacuo
6. customPurification via silica gel chromatography (Gradient: 0% to 10% ethyl acetate in heptane)

ORD record

ord-c73aac012d4a4266bfb2082ececb5e17

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09067934B2