3-Bromo-4-fluorobenzoic acid

Sodium chlorite (6.78 g, 75 mmol) and 4-fluoro-3-bromobenzaldehyde (24.63 mmol) were dissolved in 1: 1 THF/water (100 mL) and stirred vigorously at 50 oC for 5 h. EtOAc (250 mL) and IN HC1 (50 mL) was added and the layers were separated. The organic layer was washed with water (3 x 50 mL), then was extracted with 0. 5M NA2CO3 (10 x 50 mL). The combined basic aqueous layers were slowly acidified with concentrated HC1 while stirring, to precipitate the carboxylic acid product. The solid was collected via filtration and dried under high vacuum overnight (4.93 g, 91percent). A portion of the solid carboxylic acid was dissolved in chloroform (30 mL) and concentrated sulfuric acid was added. A reflux condenser was attached to the flask and the solution was heated to 55 oC. Sodium azide (2.36 g, 36.45 mmol) was added in 3 portions over 1 h. After 4 h, additional sulfuric acid (10 mL) and sodium azide (1 g) were added and the reaction was stirred at 55 oC for 16 h. The mixture was transferred to a large cooled flask and the sulfuric acid was slowly quenched with 5N sodium hydroxide. The solution was adjusted to PH-8 and the aqueous solution was extracted with DCM (5 x 30 mL). The organic extracts were dried over sodium sulfate and concentrated in vacuo to yield a dark brown oil (2.2 g, 95percent) that solidified upon standing. 1H-NMR (CDC13): δ 6.94 (t, 8.4 Hz), 6.88 (dd, 1H, J = 2.8, 5.6 Hz), 6.58 (m, 1H), 3.62 (s, 2H).3-Bromo-4-fluoro-benzaldehyde (10.0 g, 49 mmol) in [H20] (150 mL, followed by the addition [OF KMNO4] (15.5 g, [98] mmol) heated at reflux (foams extensively) for 1 h, then added additional [KMN04] (15.5 g, 98 mmol) and continued heating for another 3 h. The reaction was cooled to rt, then filtered through Celite. The solution was acidified with HC1, and the resulting white precipitate was filtered off, to afford 6.1 g (56percent) of a white solid.General procedure: Aromatic or aliphatic nitriles (2 mmol) were dissolved in 5 ml of [bmim]HSOGeneral procedure: To a mixture of acetophenone (100 mg, 1 equiv) or phenylacetylene (1 equiv) in dioxane (5 mL), Oxone (2 equiv) and TFA (2 equiv) were added. The mixture was then heated to reflux for 10 h and then cooled to r.t. H

Molecular Weight:219.01
XLogP3:2.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:217.93787
Monoisotopic Mass:217.93787
Topological Polar Surface Area:37.3
Heavy Atom Count:11
Complexity:163
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes