Dimethylamine → 3-Bromo-α-fluoro-N,N-dimethylbenzeneacetamide

Participants

Role	Name	HCID	Charge
Reactant	Dimethylamine	HCID 674	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	1071455-00-9	HCID 53410195	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	3-Bromo-α-fluoro-N,N-dimethylbenzeneacetamide	HCID 59824888	44%

Reaction Steps

A mixture of (3-bromo-phenyl)-fluoro-acetic acid (436 mg, 1.9 mmol), dimethyl amine (1.9 ml, 3.7 mmol-2M solution in THF), HATU (1.1 g, 2.8 mmol), DIEA (0.7 ml, 3.7 mmol) in DMF were stirred at room temperature overnight. The reaction was diluted with ethyl acetate, washed with 1N HCl, saturated Na2HCO3, brine, dried with Na2SO4, decanted, and concentrated to dryness. Silica chromatography of the crude using a gradient of ethyl acetate and hexane afforded 2-(3-bromo-phenyl)-2-fluoro-N,N-dimethyl-acetamide (212 mg, 44% yield). 1H NMR (500 MHz, DMSO-d6) δ 2.86 (d, 6H), 6.40-6.44 (d, 1H), 7.41 (m, 1H), 7.45 (d, 1H), 7.642 (m, 2H). MS: m/z 261.1 (M+H+).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08242280B2
Source dataset	uspto-grants-2012_08
ORD ID	ord-bf6a4297c77442e78334f657c70871d4
Source note	uspto-grants-2012_08