Ethanolamine → HCID 43085237, compound

Temperature

75 °C

A mixture of 2,6-difluorobenzyl bromide (3.7 g, 17.8 mmol) and ethanolamine (6.46 mL, 107 mmol) in ethanol (18 mL) was heated at 75° C. for 16 h. The reaction mixture was concentrated and the resulting residue was diluted with dichloromethane (50 mL). The organic layer was partitioned with water (75 mL) and the aqueous layer extracted with dichloromethane (50 mL). Combined organic layers were dried over magnesium sulfate, filtered, and concentrated to give the title compound as a yellow solid (3.25 g). (m/z): [M+H]+ calcd for C9H11F2NO, 188.08; found, 188.1. 1H NMR (d6-DMSO, 300 MHz) δ (ppm): 7.37-7.34 (m, 1H), 7.10-7.05 (m, 2H), 4.47 (t, J=5.4 Hz, 1H), 3.75 (s, 2H), 3.42 (q, J=5.5 Hz, 2H), 2.25 (t, J=5.7 Hz, 2H), 1.82 (br s, 1H).

1. concentrationThe reaction mixture was concentrated
2. additionthe resulting residue was diluted with dichloromethane (50 mL)
3. customThe organic layer was partitioned with water (75 mL)
4. extractionthe aqueous layer extracted with dichloromethane (50 mL)
5. dry with materialCombined organic layers were dried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-1873502ba001468bb198f0165e7004af

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07622508B2