2-Methoxyethanol → 2-Fluoro-1-(2-methoxyethoxy)-4-nitrobenzene

Participants

Role	Name	HCID	Charge
Reactant	2-Methoxyethanol	HCID 8019	—
Reactant	Sodium hydride	HCID 24758	—
Reactant	1,2-Difluoro-4-nitrobenzene	HCID 123053	—
Reactant	N-[3-(3-{2-[(3-Chloro-4-{[2-(dimethylamino)ethyl]oxy}phenyl)amino]-4-pyrimidinyl}pyrazolo[1,5-a]pyridin-2-yl)phenyl]-2,6-difluorobenzamide	HCID 11505567	—
Product	2-Fluoro-1-(2-methoxyethoxy)-4-nitrobenzene	HCID 23498075	—

Reaction Steps

In a procedure analogous to Example 125, 0.64 g of the title compound was prepared from 0.39 mL (4.94 mmol) of 2-methoxyethanol, 0.24 g (6.11 mmol) of a 60% mineral oil dispersion of sodium hydride, and 0.75 g (4.7 mmol) of 3,4-difluoronitrobenzene as a light yellow solid. 1H NMR (CDCl3, 400 MHz) δ 3.44 (s, 3H), 3.80 (d, 2H, J=4.6 Hz), 4.28 (t, 2H, J=4.6 Hz), 7.05 (dd, 1H, J=8.4 and 8.4 Hz), 7.98 (dd, 1H, J=10.6 and 2.7 Hz), and 8.03 (d, 1H, J=9.0 Hz).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07812022B2
Source dataset	uspto-grants-2010_10
ORD ID	ord-df06fbd9d5df41e2886216c396d687ba
Source note	uspto-grants-2010_10