2,6-DIBROMOBENZOICACID

Class white powder

2, 6-dibromobenzoic acid was synthesized according to literature procedure. See, e.g., Varcoe, J.R. et al., Chem. Mater. 2007, 19, 2686–2693, incorporated herein in its entirety. More specifically, dry tetrahydrofuran (THF, 400 mL) in a 2-neck round- bottom flask under argon was cooled to 0 °C in an ice-water bath. n-Butyllithium (2.5 M in hexanes, 117 mL) was added followed by a slow addition of diisopropylamine (45 mL) at 0 °C to form lithium diisopropylamide (LDA). The mixture was stirred for 45 min and then cooled to -78 °C in a dry ice/acetone bath. While at this temperature, 1, 3-dibromobenzene (50.0 g, 0.212 mol) was added drop-wise over 5 min and stirred for 1 h. Dry ice was then closed in a glass container and connected by syringe into the reaction mixture. After bubbling the mixture with the evolved gaseous CO was synthesized according to literature procedure. See, e.g., Varcoe, J.R. et al., Chem. Mater. 2007, 19, 2686-2693, incorporated herein in its entirety. More specifically, dry tetrahydrofuran (THF, 400 mL) in a 2-neck round- bottom flask under argon was cooled to 0 C in an ice-water bath. n-Butyllithium (2.5 M in hexanes, 117 mL) was added followed by a slow addition of diisopropylamine (45 mL) at 0 C to form lithium diisopropylamide (LDA). The mixture was stirred for 45 min and then cooled to -78 C in a dry ice/acetone bath. While at this temperature, 1, 3-dibromobenzene (50.0 g, 0.212 mol) was added drop-wise over 5 min and stirred for 1 h. Dry ice was then closed in a glass container and connected by syringe into the reaction mixture. After bubbling the mixture with the evolved gaseous CO2 for 45 min, pieces of dry ice were added into the mixture. The mixture was allowed to slowly warm up to room temperature. Aqueous sodium hydroxide (0.5 M) and ethyl acetate (400 mL) were added until all of the solid was dissolved. The aqueous layer was washed with ethyl acetate and then acidified with concentrated hydrochloric acid until approximately pH=1. The precipitate was dissolved in fresh ethyl acetate, washed with brine, dried over MgSO4, filtered, and the solvent was evaporated at 40 C under vacuum. The oil was cooled to room temperature, resulting in crystallization. The solid was boiled in hexanes (2 L) for 1 h and then cooled to room temperature. The solid was collected, washed with hexanes, and dried under vacuum at 80 C, resulting in 1 (39.3 g, 66%) as an off-white powder. 1H NMR (500 MHz, DMSO-d6, delta 7.70 (d, J = 8.1 Hz, 2H), 7.29 (t, J = 8.1 Hz, 1H).13C NMR (125 MHz, DMSO-d6, delta 166.87, 138.67, 131.87, 131.65.

Molecular Weight:279.91
XLogP3:3.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:279.85576
Monoisotopic Mass:277.85780
Topological Polar Surface Area:37.3
Heavy Atom Count:11
Complexity:151
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes