2-Bromo-6-fluorobenzoicacid

White powder

Adapted from a literature procedure.[36] To a flask containing anhydrous diisopropylamine (9.24 mL, 66 mmol) in dry THF (300 mL) at -30 C, n-BuLi (1.6 M in hexane, 41.3 mL, 66 mmol) was added dropwise. The mixture was then cooled to -78 C, and 3-bromofluorobenzene (9) (6.6 mL, 60 mmol) was slowly added. After 2 h of reaction at this temperature, the reaction mixture was quenched with dry ice. Stirring was maintained for 3 h, and the mixture was then slowly allowed to warm to room temperature (rt), and hydrolyzed with water (300 mL). The aqueous layer was washed with ether (2x150 mL), acidified with 2M HCl (pH 1–2), and extracted with ether (3x150 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under vacuum. Purification of the residue by recrystallization (cyclohexane/ethylacetate) afforded 6-bromo-2-fluorobenzoic acid (10) as awhite solid (11.8 g, 90 percent), mp 154–155 C (lit. 152–1548C[37]). nmax (neat)/cm1 2872, 2665, 1696, 1600, 1449, 1297.dH (CDCl3, 400 MHz) 7.45 (1H, d, J 8.1), 7.32 (1H, dt, J 8.4, 5.8), 7.14 (1H, dd, J 9.4, 1.1). dC (100 MHz, [D6]DMSO) 164.6, 158.2 (d, J 250.0), 132.1 (d, J 8.9), 128.6, 125.7 (d, J 22.0), 118.6(d, J 5.1), 115.1 (d, J 21.2).A solution 2-bromo-6-fluorobenzonitrile 10 in KOH 1M (25mL) was stirred to reflux for 2 day. The reaction was cooled to room temperature and the HCl concentrate was added to pH=2-3. The aqueous solution was extracted with ethyl acetate (3 times). The organic layer was separated, dried and evaporated to obtain the desired product (126mg, yield: 95percent>). CA solution 2-bromo-6-fluorobenzonitrile 10 in KOH 1M (25mL) was stirred to reflux for 2 day. The reaction was cooled to room temperature and the HC1 concentrate was added to pH=2-3. The aqueous solution was extracted with ethyl acetate (3 times). The organic layer was separated, dried and evaporated to obtain the desired product (126mg, yield: 95percent). C7H4BrF02, MS-ESI: [M-H] -218m/z. 1H-NMR: (CDC13, 400MHz) δ 7.14 (t, 1H, Jo=8.4Hz, H-4), 7.29-7.35 (m, 1H, H-3), 7.45 (d, 1H, H-5).

Molecular Weight:219.01
XLogP3:1.3
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