Dimethylformamide → HCID 59199282, compound

Temperature

-78 °C

2,6-Dibromo-4-(trifluoromethyl)aniline (3.19 g, 10.0 mmol, 1.00 eq) was dissolved in THF (50 mL) and cooled to −78° C. A 2.5 M solution of n-butyllithium in hexanes (8.40 mL, 21.0 mmol, 2.10 eq) was added dropwise over 15 min. The mixture was stirred at −78° C. for 1 h. A solution of DMF (1.03 mL, 14.0 mmol, 1.40 eq) in THF (5 mL) was added, and the mixture was stirred an additional 1 h at −78° C. The reaction was allowed to come to −15° C. over 30 min and then quenched with brine. The mixture was diluted with ethyl acetate, washed sequentially with water and brine, dried over sodium sulfate, filtered, and concentrated to give 1.74 g of the desired product as a pale yellow, crystalline solid. ES/MS m/z 268, 270 (MH+).

1. stirringthe mixture was stirred an additional 1 h at −78° C
2. waitto come to −15° C. over 30 min
3. customquenched with brine
4. additionThe mixture was diluted with ethyl acetate
5. washwashed sequentially with water and brine
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-00e57b465e4e4571877bcac18996ee2d

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07932262B2