3-Bromothiophene-2-carboxylicacid

white to light yellow crystal powder

To a solution of nBuLi (2.5 M, 0.055 mol, 22 ml) in dry Et[0526] 3-Bromo-thiophene-2-carboxylic acid. To a solution of 3-bromothiophene (600.0 g, 3.68 mol) in THF (3 L) cooled to -72° C. was added LDA (1.93 L, 3.86 mol, 2 N) slowly over 2 hours. The rate of LDA addition is such that the reaction temperature never exceeded -68° C. After complete addition, the solution is stirred for an additional 40 minutes. Diethyl ether (3 L) is then added via an addition funnel such that the temperature is maintained below -65° C. The addition funnel is then replaced with a dispersion tube and CO2 gas is bubbled through the solution for 3 hours. Dry ice (500 g) is then added and the mixture is stirred overnight. The reaction flask is then placed in an ice bath and 6 N HCl is added slowly to prevent excessive bubbling until the pH of the solution is adjusted to 1-2. The resulting mixture is then extracted with EtOAc. The extract is washed with brine then dried over MgSO4, filtered and evaporated. The product is dried under vacuum at room temperature yielding 585.15 g (77percent) as an off-white solid.a. A mixture of S-bromo-thiophene-l-carboxylic acid (2.2g, lO.betammol), 4N HCl (in dioxane, ImI), H2SO4 (98%, 0.2ml) and methanol (30ml) was heated under reflux for 24h, cooled to room temperature, diluted with ethyl acetate, washed withwater, aq. NaHCO3, half- sat.-aq. NaCl twice, dried (MgSO4) and concentrated to dryness to give compound 23G (100%) directly used in next step.By refluxing Preparation 8 4-(2-Hydroxymethylthiophen-3-yl)piperidine-1-carboxylic Acid t-Butyl Ester 3-Bromothiophene-2-carboxylic acid (5.0 g, 24 mmol, 1 eq.) was dissolved in MeOH (100 mL) and the mixture was degassed and purged with nitrogen (2*). SOCl2 (15 mL, 0.2 mol, 8.3 eq.) was added dropwise and the resulting mixture was stirred overnight at room temperature. The mixture was then concentrated and DCM (150 mL) was added. Saturated NaHCO3 (20 mL) was added, and the resulting mixture was stirred at room temperature for 15 minutes. The organic layer was washed with saturated NaHCO3 (20 mL), water (20 mL), and saturated aqueous NaCl (20 mL), then dried over Na2SO4, filtered and concentrated to yield The

Molecular Weight:207.05
XLogP3:2.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:205.90371
Monoisotopic Mass:205.90371
Topological Polar Surface Area:65.5
Heavy Atom Count:9
Complexity:128
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes