2-(2,2-Dibromo-vinyl)-phenylamine could be produced through the following synthesis routes.

A. 1-(2,2-Dibromoethenyl)-2-nitrobenzene. A 500-mL, three-necked round-bottomed flask equipped with a magnetic stirring bar and fitted with a 125-mL pressure-equalizing addition funnel (capped with a rubber septum), a thermometer and a two-tap Schlenk adaptor connected to a bubbler and an argon/vacuum manifold is sequentially charged at room temperature with 2-nitrobenzaldehyde (4.03 g, 26.4 mmol, 1.0 equiv) and tetrabromomethane (13.13 g, 39.5 mmol, 1.5 equiv). (100 mL) is added into the flask using the addition funnel and the system is purged with argon for 5 min. The addition funnel is capped with a rubber septum, and the reaction is kept under argon atmosphere. The resulting yellow solution is cooled to 2-3 °C (internal temperature) with an ice-bath. The addition funnel is re-charged with dichloromethane (20 mL), and then (15.9 mL, 58 mmol, 2.2 equiv) is added via syringe through the septum and the resulting solution is added dropwise to the stirred mixture in the flask over a period of 60 min. During the addition of triisopropyl phosphite the internal temperature of the flask is maintained between 3 and 5 °C. The mixture is then stirred (internal temperature, 3 °C) until the starting material has been completely consumed as shown by thin layer chromatography (TLC), at which point the mixture is quenched with sodium bicarbonate (saturated aqueous solution, 85 mL) added through the addition funnel with the stopcock open. The mixture is transferred into a 500-mL separatory funnel and the organic phase separated. The aqueous phase is extracted further with dichloromethane (2 × 40 mL) and the combined organic phase is washed once with water (80 mL), transferred into a 500-mL, one-necked, round-bottomed flask and concentrated by rotary evaporation (35 °C, 15 mmHg) to give 27.0-28.5 g of a brown oil. The flask containing the crude material is equipped with a water-cooled condenser. Concentrated HCl (12 M, 30 mL) and glacial acetic acid (30 mL) are added, the condenser is capped with a two-tap Schlenk adaptor connected to a bubbler and an argon/vacuum manifold, and the resulting mixture is heated to reflux in an oil bath (110 °C external temperature) and stirred for 14 h under an argon atmosphere. The reaction is then cooled to room temperature and distilled water (150 mL) is added. The mixture is neutralized by the portion-wise addition of sodium carbonate (45 g, 0.36 mol). Diethyl ether (150 mL) is added, the contents of the flask are stirred vigorously for 5 min and any solids are removed by vacuum filtration (water aspirator, 20 mbar) through a fritted glass funnel (8.0 cm diameter, porosity 3). The residue is washed with diethyl ether (2 × 20 mL), the filtrate is poured into a 500-mL separatory funnel and the phases are separated. The aqueous phase is extracted with diethyl ether (2 × 100 mL). The combined organic phases are washed with distilled water (2 × 100 mL) and brine (75 mL), dried (MgSO₄), filtered (gravity filtration through a fluted filter paper) and concentrated under reduced pressure with a rotary evaporator (30 °C, 15 mmHg) to give 8.01-8.06 g (99 %) of a brown oil, which solidified under high vacuum (0.04 mmHg). A stir bar is inserted into the flask, heptane (15 mL) is added, and the flask is heated with stirring to 50 °C in an oil bath (external temperature). (1 mL) is added, and the solution is decanted into a second 50-mL, round-bottomed flask which is pre-warmed to at least 50 °C to remove any insoluble material. The flask is placed in the oil bath, which is allowed to cool slowly. When the temperature of the oil bath has reached 40 °C, the flask is scratched to induce crystallization. The flask is then allowed to cool to room temperature, left at room temperature for 1 h and then cooled to 4 °C (refrigerator) for a further 14 h. The product is isolated by vacuum filtration through a fritted glass funnel (3 cm diameter, porosity 4). The crystals are washed with ice-cold heptane (2 × 5 mL) and then dried under vacuum (0.03 mmHg, 14 h) to afford pure 1-(2,2-dibromoethenyl)-2-nitrobenzene (5.95-6.11 g, 73-75 %) as a brown crystalline solid.

B. 2-(2,2-Dibromo-vinyl)-phenylamine. A 250-mL Büchi autoclave glass vessel is charged with 1-(2,2-dibromovinyl)-2-nitrobenzene (5.80 g, 18.9 mmol) and methanol (100 mL). The solution is stirred until all of the solid is dissolved, at which point vanadium-doped platinum on activated carbon is added (580 mg, 0.015 mmol, 8.0 × 10-4 equiv). The vessel is attached to the autoclave and pressurized to 2.5 bar with hydrogen. The flask is thrice evacuated (via diaphragm pump) and back-filled with hydrogen to 2.5 bar, then stirred for 3 h at room temperature. The hydrogen is removed by evacuation, and the suspension is filtered through a pad of celite (2.5 cm in height). The pad is washed with methanol (3 × 80 mL), and the filtrate is concentrated on a rotary evaporator (30 °C, 15 mmHg) and dried under vacuum (0.03 mmHg, 16 h) to afford 5.22 g (99.8 %) of the title compound as an orange oil.