ChemicalBook CAS DataBase List 2-Bromo-6-fluorobenzonitrile

2-Bromo-6-fluorobenzonitrile synthesis

5synthesis methods

Product Name:2-Bromo-6-fluorobenzonitrile
CAS Number:79544-27-7
Molecular formula:C7H3BrFN
Molecular Weight:200.01

2-Amino-6-fluorobenzonitrile (18.0 g, 132 mmol) was dissolved in hot 1,4-dioxane (20 ml), 48% hydrobromic acid (200 ml) was added and the mixture cooled to 0°C before dropwise addition of sodium nitrite (10.5 g, 152 mmol) in water (20 ml) over 1.5 h. The resulting mixture was stirred at 0°C for 1.5 h then poured onto a cooled (0°C) solution of copper(I) bromide (56.8 g, 396 mmol) in 48% hydrobromic acid (50 ml). The solution was stirred at 0°C for 15 min then heated at 50°C for 20 min. The mixture was cooled to ambient temperature, diluted with water (1200 ml) and extracted with ethyl acetate (2 x 400 ml). The combined organics were washed with 10% aqueous ammonia solution (400 ml), water (400 ml) and brine (500 ml), dried over anhydrous magnesium sulfate, filtered and evaporated to give an orange oil. Purification by chromatography on silica 5 gel eluting with isohexane on a gradient of ethyl acetate (2-4%) gave 2-bromo-6-fluorobenzonitrile. White solid, yield (18.5 g, 70%). δH (400 MHz, CDCl3) 7.17-7.23 (1H, ddd, J 8, 8 and 1), 7.44-7.52 (2H, m).
synthesis of 2-Bromo-6-fluorobenzonitrile

synthesis of 2-Bromo-6-fluorobenzonitrile

360575-28-6 Synthesis

360575-28-6
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79544-27-7
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Yield:79544-27-7 152 g

Reaction Conditions:

with formic acid;hydroxylamine hydrochloride at 100; for 2 h;

Steps:

2.b b) Synthesis of 2-fluoro-6-bromobenzonitrile:

165 g of 2-fluoro-6-bromobenzaldehyde, 114 g of hydroxylamine hydrochloride and 450 g of formic acid were added to a 2 L single-necked flask and heated at 100 ° C for 2 hours. Distillation of formic acid, with sodium carbonate aqueous solution to adjust the pH value of 7 or so.Ethyl acetate was added to extract the oil layer, and 152 g of 2-fluoro-6-bromobenzonitrile was distilled off under reduced pressure,GC purity 98%.

References:

CN106977535,2017,A Location in patent:Paragraph 0030