4-Bromo-2-fluoroaniline

solid

This compound was prepared followinga literature procedure.39 To a suspension of 2-fluoroaniline (12)(2.22 g, 20 mmol) in CHCl3 (50 mL) was added NBS (3.56 g, 20 mmol), and the resulting mixture was stirred at RT for 2 h. After completionmonitored by TLC, the mixture was quenched with sat. Na2S2O3 (aq.)and extracted with CH2Cl2 (3×20 mL). The combined organic layerswere dried over MgSO4 and concentrated in vacuo. The crude productwas purified by flash chromatography (hexane/ethyl acetate 10:1) togive the product 13 as an orange oil (3.42 g, 90percent); Rf (hexane/ethylacetate 6:1): 0.35; 1H NMR (300 MHz, CDCl3): δ 7.14 (1H, dd, J=2.1, 10.5 Hz), 7.05 (1H, d, J=8.4 Hz), 6.65 (1H, t, J=9.0 Hz), 3.72 (2H, br.s); 13C NMR (75 MHz, CDCl3): δ 151.5 (d, JCF=241.5 Hz), 133.9 (d, JCF=12.8 Hz), 127.5 (d, JCF=3.0 Hz), 118.8 (d, JCF=21.8 Hz), 117.9(d, JCF=3.8 Hz), 109.0 (d, JCF=9.0 Hz). The spectroscopic datamatched that reported in the literature.39Synthesis: To a 250 mL three-necked flask were added 7.1 g (0.022 mol) of tetrabutylammonium bromide, 22.2 g (0.20 mol) of o-fluoroaniline and 50 mL of methylene chloride, stirred until all dissolved, and the controlled temperature was lower than 30 ° C (0.21 mol) of bromine was slowly added dropwise over about 30 to 60 minutes, after which the temperature of the material was raised to reflux (about 40 ° C) for about 2.5 hours. Post-treatment: The mixture was cooled to room temperature, filtered, and the filter cake was washed twice with 20 x 2 mL of dichloromethane, followed by dispersing the filter cake in 50 mL of dichloromethane and adding about 80 g of 10percent sodium hydroxide solution To pH = 7 to 8, and the organic phase was allowed to stand apart. The organic phase was washed twice with 50 x 2 mL of deionized water and the solvent was distilled off to give 34.3 g (theoretical 38 g) of 4-bromo-2-fluoroaniline.Gas chromatographic analysis showed that the product content was 94.8percent and the yield was 85.6percent.Under room temperature, will be 2-fluoro aniline (3.0 g, 27.0 mmol) dissolved in DMF (15 ml) in. Under nitrogen protection and ice in a mixture obtained to the slowly dropping N-bromo succinimide (5.3 g, 29.7 mmol) of a solution of DMF (15 ml). After the completion of the dropping, the obtained reaction mixture in the 1 hour. Furthermore, the obtained mixture into ice water (100 ml) in. The resulting mixture is extracted with ethyl acetate. The resulting organic phase is concentrated under reduced pressure to obtain 5.0 g brown oily, without purification directly used for the next step reaction.

4-Bromo-2-fluoroaniline is a useful research chemical. Application 4-Bromo-2-fluoroaniline is an organic synthesis intermediate and pharmaceutical intermediate, in the process of organic synthesis and pharmaceutical research and development.

Molecular Weight:190.01
XLogP3:2.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:188.95894
Monoisotopic Mass:188.95894
Topological Polar Surface Area:26
Heavy Atom Count:9
Complexity:99.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes